Publications

2023

  1. Lukin, A.; Komarova, K.; Vinogradova, L.; Rogacheva, E.; Kraeva, L.; Krasavin, M. Synthesis and antibacterial evaluation of ciprofloxacin congeners with spirocyclic amine periphery. Int. J. Mol. Sci. 2023, 24, 954
  2. Dar'in, D.; Kantin, G.; Glushakova, D.; Sharoyko, V.; Krasavin, M. Diazo Tetramic Acids Provide Access to Natural-Like Spirocyclic Δα,β-Butenolides through Rh(II)-catalyzed O-H Insertion/Base-Promoted Cyclization. J. Org. Chem., accepted 26.12.2022
  3. Krivovicheva, V.; Bubyrev, A.; Kalinin, S.; Dar'in, D.; Gureev, M.; Vullo, D.; Krasavin, M.; Korsakov, M.; Supuran, C. T. A new way of synthesizing heterocyclic primary sulfonamide probes for carbonic anhydrase. Mendeleev Commun., accepted 23.12.2022
  4. Krasavin, M.; Adamchik, M.; Bubyrev, A.; Heim, C.; Maiwald, S.; Zhukovsky, D.; Zhmurov, P.; Bunev, A.; Hartmann, M. D. Synthesis of novel glutarimide ligands for the E3 ligase substrate receptor Cereblon (CRBN): investigation of their binding mode and antiproliferative effects against myeloma cell lines. Eur. J. Med. Chem. 2023, 246, 114990
  5. Lukin, A.; Vinogradova, L.; Komarova, K.; Krasavin, M. Spirocyclic azetidines for drug discovery: novel Boc-protected 7'H-spiro[azetidine-3,5'-furo[3,4-d]pyrimidines]. Mendeleev Commun. 2022, accepted 10.11.2022
  6. Lukin, A.; Vinogradova, L.; Komarova, K.; Kalinin, S.; Krasavin, M. Synthesis of 1-oxa-9-azaspiro[5.5]undecane-9-sulfonamides bearing a diverse molecular periphery and a rare zinc-binding group for carbonic anhydrase interrogation. Mendeleev Commun., accepted 01.11.2022
  7. Solovyev, I.; Dar'in, D.; Krasavin, M. Synthetic enabling of spirocyclic oxetane fatty acid mimetics based on 1-oxa-6,7-diazaspiro[3.4]oct-7-en-5-one scaffold via diazo chemistry. Mendeleev Commun. 2023, 33, 21-23
  8. Lukin, A.; Komarova, K.; Vinogradova, L.; Rogacheva, E.; Kraeva, L.; Dogonadze, M.; Vinogradova, T.; Krasavin, M. Urea derivatives of spirocyclic piperidines endowed with antibacterial activity. Mendeleev Commun. 2023, 33, 109-111
  9. Adamchik, M.; Bubyrev, A.; Zhukovsky, D.; Zhmurov, P.; Bunev, A.; Krasavin, M. Synthesis of novel glutarimide derivatives via the Michael addition of (hetero)aromatic thiols: pronounced effect of sulfur oxidation on cytotoxicity towards multiple myeloma cell lines. Mendeleev Commun. 2023, 33, 67-69
  10. Sibinčić, N.; Kalinin, S.; Sharoyko, V.; Efimova, J.; Gasilina, O. A.; Korsakov, M.; Gureev, M.; Krasavin, M. A Series of Trifluoromethylisoxazolyl- and Trifluoromethylpyrazolyl-Substituted (Hetero)aromatic Sulfonamide Carbonic Anhydrase Inhibitors: Synthesis and Convenient Prioritization Workflow for Further In Vivo studies. Med. Chem. 2023, 19, 193-210

2022

  1. Moshnenko, N.; Kazantsev, A.; Bakulina, O.; Dar'in, D.; Krasavin, M. The Use of Aryl-Substituted Homophthalic Anhydrides in the Castagnoli–Cushman Reaction Provides Access to Novel Tetrahydroisoquinolone Carboxylic Acid Bearing an All-Carbon Quaternary Stereogenic Center. Molecules 2022, 27, 8462
  2. Lebedev, R.; Dar'in, D.; Kantin, G.; Bakulina, O.; Krasavin, M. One-pot sequence of Staudinger/aza-Wittig/Castagnoli-Cushman reactions provides facile access to novel natural-like polycyclic ring system. Molecules 2022, 27, 8130
  3. Paramonova, P.; Lebedev, R.; Bakulina, O.; Dar'in, D.; Krasavin, M. In situ generation of imines by Staudinger/aza-Wittig tandem combined with thermally induced Wolff rearrangement for one-pot three-component β-lactam synthesis. Org. Biomol. Chem. 2022, 20, 9679-9683
  4. Vepreva, A.; Yanovich, A.; Dar'in, D.; Kantin, G.; Bunev, A.; Krasavin, M. Novel spirocyclic scaffold accessed via tandem Claisen rearrangement – intramolecular oxa-Michael addition. Beilstein J. Org. Chem. 2022, 18, 1649-1655
  5. Malkova, K.; Bubyrev, A.; Krivovicheva, V.; Dar'in, D.; Bunev, A.; Krasavin, M. Novel Bis-Triazole Scaffold Accessed via Two Tandem [3+2] Cycloaddition Events Including an Uncatalyzed, Room-Temperature Azide-Alkyne Click Reaction. Beilstein J. Org. Chem. 2022, 18, 1636–1641
  6. Krasavin, M.; Lukin, A.; Sukhanov, I.; Gerasimov, A.; Kuvarzin, S.; Efimova, E. V.; Dorofeikova, M.; Nichugovaskaya, A.; Matveev, A.; Onokhin, K.; Zakharov, K.; Gureev, M.; Gainetdinov, R. R. Discovery of Trace Amine Associated Receptor 1 (TAAR1) Ag-onist 2-(5-(4'-Chloro-[1,1'-biphenyl]-4-yl)-4H-1,2,4-triazol-3-yl)ethan-1-amine (LK00764) for the Treatment of Psychotic Disorders. Biomolecules 2022, 12, 1650
  7. Krivovicheva, V.; Bubyrev, A.; Kalinin, S.; Dar'in, D.; Krasavin, M. Synthetic Exploration of Novel Sulfamoyl Cyanide N-Oxides in Heterocycle Synthesis. Eur. J. Org. Chem. 2022, e202201162
  8. Malkova, K.; Bubyrev, A.; Balalaie, S.; Dar'in, D.; Krasavin, M. Metal-free synthetic approaches to 1,5-disubstituted 1,2,3-triazoles. Tetrahedron Lett. 2022, 112, 154228
  9. Guranova, N.; Yakovleva, L.; Bakulina, O.; Dar'in, D.; Krasavin, M. Extending the scope of the new variant of the Castagnoli-Cushman cyclocondensation onto o-methyl benzoic acids bearing various electron-withdrawing groups in the α-position. Molecules 2022, 27, 7211
  10. Bannykh, A.; Levashova, E.; Bakulina, O.; Krasavin, M. New Reagent Space and New Scope for the Castagnoli-Cushman Reaction of Oximes. Org. Biomol. Chem. 2022, 20, 8643–8648
  11. Krasavin, M.; Peshkov, A. A.; Lukin, A.; Komarova, K.; Vinogradova, L.; Smirnova, D.; Kanov, E. V.; Kuvarzin, S. R.; Murtazina, R. Z.; Efimova, E. V.; Gureev, M.; Onokhin, K.; Zakharov, K.; Gainetdinov, R. R. Discovery and In Vivo Efficacy of Trace Amine-Associated Receptor 1 (TAAR1) Agonist 4-(2-Aminoethyl)-N-(3,5-dimethylphenyl)piperidine-1-carboxamide Hydrochloride (AP163) for the Treatment of Psychotic Disorders. Int. J. Mol. Sci. 2022, 23, 11579
  12. Lavit, K.; Sapegin, A.; Linnik, S.; Ryazantsev, M.; Krasavin, M. Steric Push Towards the [n+3] Hydrated Imidazoline Ring Expansion (HIRE) of Dibenzo[1.4]oxazepines and Thiazepines. Eur.J. Org.Chem. 2022, e202200818
  13. Sapegin, A.; Rogacheva, E.; Kraeva.; Gureev, M.; Dogonadze, M.; Vinogradova, T.; Yablonsky, P.; Balalaie, S.; Baykov, S. V.; Krasavin, M. Novel 5-Nitrofuran-Tagged Imidazo-Fused Azines and Azoles Amenable by the Groebke-Blackburn-Bienaymé Multicomponent Reaction: Activity Profile against ESKAPE Pathogens and Mycobacteria. Biomedicines 2022, 10, 2203
  14. Lukin, A.; Chudinov, M.; Rogacheva, E.; Kraeva, L.; Bakulina, O.; Krasavin, M. Exploration of spirocyclic derivatives of ciprofloxacin as antibacterial agents. Molecules 2022, 27, 4864
  15. Barkhatova, D.; Zhukovsky, D.; Heim, D.; Maiwald, S.; Hartmann, M. D.; Krasavin, M. Synthesis of novel glutarimide derivatives via the Ugi multicomponent reaction: affinity towards the E3 ubiquitin ligase substrate receptor Cereblon. Mendeleev Commun. 2022, 32, 747-749
  16. Dar'in, D.; Kantin, G.; Bunev, A.; Krasavin, M. Facile and Diastereoselective Arylation of the Privileged 1,4-Dihydroisoquinolin-3(2H)-one Scaffold. Beilstein J. Org. Chem. 2022, 18, 1070-1078
  17. Kazantsev, A.; Bakulina, O.; Dar'in, D.; Kantin, G.; Bunev, A.; Krasavin, M. Unexpected Ring Contraction of Homophthalic Anhydrides Under Diazo Transfer Conditions. Org. Lett. 2022, 24, 4762-4765
  18. Bakulina, O.; Bannykh, A.; Levashova, E.; Krasavin, M. Conjugates of Iron-Transporting N-Hydroxylactams with Ciprofloxacin. Molecules 2022, 27, 3910
  19. Bakulina, O.; Sapegin, A.; Bunev, A.; Krasavin, M. Synthetic Approaches to Constructing Proteolysis Targeting Chimeras (PROTACs). Mendeleev Commun. 2022, 32, 419-432
  20. Zhukovsky, D.; Kanov, E.; Gainetdinov, R.; Krasavin, M. Synthesis of a Library of 2-Aryl-2H-tetrazole-5-carboxamides for Photoaffinity Labeling of Aminergic G-Protein Coupled Receptors. Mendeleev Commun. 2022, 32, 604–605
  21. Gapanenok, D.; Makhmet, A. Peshkov, A. A.; Smirnova, D.; Amire, N.; Peshkov, V. A.; Spiridonova, D.; Dar'in, D.; Balalaie, S.; Krasavin, M. Multicomponent Assembly of Trisubstituted Imidazoles and Their Photochemical Cyclization into Fused Polyheterocyclic Scaffolds. J. Org. Chem. 2022, 87, 7838-7851
  22. Vepreva, A.; Bunev, A. S.; Kudinov, A. Yu.; Kantin, G.; Krasavin, M.; Dar'in, D. Unusual Highly Diastereoselective Rh(II)-catalyzed Dimerization of Diazo Arylidene Succinimides Provides Access to New Dibenzazulene Scaffold. Beilstein J. Org. Chem. 2022, 18, 533–538
  23. Krasavin, M.; Jovanović, M.; Podolski-Renić, A.; Pešić, M. The role of the thioredoxin detoxification system in cancer progression and resistance. Front. Mol. Biosci. 2022, 8, 883297
  24. Ananeva, A.; Bakulina, O.; Dar'in, D.; Kantin, G.; Krasavin, M. Dicarboxylic Acid Monoesters in β- and δ-Lactam Synthesis. Molecules 2022, 27, 2469
  25. Kalinin, S.; Kovalenko, A.; Valtari, A.; Nocentini, A.; Gureev, M.; Urtti, A.; Korsakov, M.; Supuran, C. T.; Krasavin, M. 5-(Sulfamoyl)thien-2-yl 1,3-Oxazole Inhibitors of Carbonic Anhydrase II with Hydrophilic Periphery. J. Enzyme Inhib. Med. Chem. 2022, 37, 1005-1011
  26. Krasavin, M.; Shetnev, A.; Panova, V.; Ivanovskyi, S.; Kalinin, S.; Vinogradova, T.; Sharoyko, V.; Yablonsky, P. Hetaryl- and heteroarylvinyl-substituted nitrofurans identified as non-cytotoxic selective antitubercular agents. Mendeleev Commun. 2022, 32, 452-453
  27. Zhukovsky, D.; Dar'in, D.; Bakulina, O. Krasavin, M. Preparation and synthetic applications of five-to-seven-membered cyclic α-diazo monocarbonyl compounds. Molecules 2022, 27, 2030
  28. Grintsevich, S.; Sapegin, A.; Krasavin, M. Heteroatom is not needed: access to dibenzo[e,h][1,4]diazecin-9-ones from dibenzo[b,e]azepin-6-one via the hydrated imidazoline ring expansion (HIRE) approach. Tetrahedron Lett. 2022, 94, 153718
  29. Sharonova, T.; Zhmurov, P.; Kalinin, S.; Nocentini, A.; Angeli, A.; Ferraroni, M.; Korsakov, M.; Supuran, C.; Krasavin, M. Diversely Substituted Sulfamides for Fragment-Based Drug Discovery of Carbonic Anhydrase Inhibitors: Synthesis and Inhibitory Profile. J. Enzyme Inhib. Med. Chem. 2022, 37, 857–865
  30. Chupakhin, E. G.; Krasavin, M. Natural compounds as inhibitors of thioredoxin reductase (TrxR1). Russ. Chem. Bull. 2022, 71, 443–448
  31. Chupakhin, E. G.; Kantin, G. P.; Dar’in, D. D.; Krasavin, M. Novel chromeno[2,3-c]pyrroles synthesized via intramolecular rhodium(II) carbene trapping. Mendeleev Commun. 2022, 32, 382-383
  32. Geyl, K. K.; Baykov, S. V.; Kalinin, S. A.; Bunev, A. S.; Troshina, M. A.; Sharonova, T. V.; Skripkin, M. Y.; Kasatkina, S. O.; Presnukhina, S. I.; Shetnev, A. A.; Krasavin, M. Y.; Boyarskiy, V. P. Synthesis, structure, and antiproliferative action of 2-pyridyl urea-based Cu(II) complexes. Biomedicines 2022, 10, 461
  33. Guranova, N.; Bakulina, O.; Dar'in D.; Kantin, G.; Krasavin, M. Homophthalic Esters: A New Type of Reagents for the Castagnoli-Cushman Reaction. Eur. J. Org. Chem. 2022, e202101281
  34. Paramonova, P.; Bakulina, O.; Nabiyev, A.; Dar'in, D.; Krasavin, M. The Castagnoli-Cushman reaction of 3-aryl glutaric acids: a convenient, diastereoselective entry into medicinally important 6-oxo-2,4-diarylpiperidine-3-carboxylic acid scaffold. ChemistrySelect 2022, 7, e202104011
  35. Zhukov, A. S.; Khairutdinov, V. R.; Samtsov, A. V.; Krasavin, M.; Garabadzhiu, A. V. Preclinical Efficacy Investigation of Human Neutrophil Elastase Inhibitor Sivelestat in Animal Model of Psoriasis. Skin Health Dis. 2022, 2, e90
  36. Grintsevich, S.; Sapegin, A.; Krasavin, M. Significant Broadening of the Substrate Scope for the Hydrated Imidazoline Ring Expansion (HIRE) via the Use of Lithium Hexamethyldisylazide. Synthesis 2022, 54, 2494-2510
  37. Vepreva, A.; Kantin, G.; Krasavin, M.; Dar'in. A General Way to Spiro-Annulated 2-Benzoxepines via Rh2(esp)2-catalyzed [5+2] Cycloaddition of Diazo Arylidene Succinimides to Ketones. Synthesis 2022, 54, 5128-5138
  38. Peshkov, A. A.; Makhmet, A.; Bakulina, O.; Kanov, E.; Gainetdinov, R.; Peshkov, V. A.; Dar'in, D.; Krasavin, M. A general approach to spirocyclic piperidines via Castagnoli-Cushman chemistry. Synthesis 2022, 54, 2604-2615
  39. Paramonova, P.; Sharonova, S.; Kalinin, S.; Chupakhin, E.; Bunev, A.; Krasavin, M. (E)-3-Arylidene-4-diazopyrrolidine-2,5-diones conveniently elaborated into cytotoxic compounds bearing a primary sulfonamide and a Michael acceptor moieties. Mendeleev Commun. 2022, 32, 176-177
  40. Krasavin, M.; Bubyrev, A.; Kazantsev, A.; Heim, C.; Maiwald,S.; Zhukovsky, D.; Dar'in, D.; Hartmann, M. D.; Bunev, A. Replacing the Phthalimide Core in Thalidomide with Benzotriazole. J. Enzyme Inhib. Med. Chem. 2022, 37, 527-530
  41. Kazantsev, A.; Krasavin, M. Ligands for Cereblon: 2017–2021 Patent Overview. Exp. Opin. Ther. Pat. 2022, 32, 171-190
  42. Grintsevich, S.; Sapegin, A.; Duszyńska, B.; Bojarski, A. J.; Krasavin, M. An attempt at the hydrated imidazoline ring expansion (HIRE) of diarene-fused [1,4]diazepinones delivers selective dopamine D2 receptor ligands. Synthesis 2022, 54, 658-666
  43. Firsov, A.; Bakulina, O.; Dar´in, D.; Sokolov, V.; Krasavin, M. Synthesis of γ-sultam-annelated δ-lactams via the Castagnoli-Cushman reaction of sultam-based dicarboxylic acids. J. Org. Chem. 2022, 87, 1537-1540

2021

  1. Kalinin, S.; Malkova, A.; Sharonova, T.; Sharoyko, V.; Bunev, A.; Supuran, C. T.; Krasavin, M. Carbonic anhydrase IX inhibitors as candidates for combination therapy of solid tumors. Int. J. Mol. Sci. 2021, 22, 13405
  2. Budeev, A.; Kantin, G.; Dar'in, D.; Krasavin, M. Ugi reaction-derived 1H-pyrrol-2(5H)-ones proved as valid precursors to a new class of heterocyclic α-diazocarbonyl compounds. Tetrahedron Lett. 2021, 89, 153598
  3. Levashova, E.; Bakulina, O.; Dar'in, D.; Krasavin, M. Catalyst-Free Synthesis of Diastereomerically Pure 3-Cyanoazetidin-2-ones via Thermally Promoted Tandem Wolff Rearrangement–Staudinger [2+2] Cycloaddition. ChemistrySelect 2021, 6, 13582-13588
  4. Bubyrev, A.; Malkova, K.; Kantin, G.; Dar´in, D.; Krasavin, M. Metal-free synthesis of 1,5-disubstituted 1,2,3-triazoles. J. Org. Chem. 2021, 86, 17516-17522
  5. Krasavin, M.; Dar'in, D.; Balalaie, S. Post-condensational modifications of the Groebke‐Blackburn‐Bienaymé reaction products for scaffold-oriented synthesis. Tetrahedron Lett. 2021, 86, 153521
  6. Bakulina, O.; Inyutina, A.; Dar'in, D.; Krasavin, M. Multicomponent Reactions Involving Diazo Reagents: A 5-Year Update. Molecules 2021, 26, 6563
  7. Chupakhin, E.; Bakulina, O.; Dar'in, D.; Krasavin, M. Facile entry into the 1H-pyrrolo[3,4-b]indolizine-1,3(2H)-dione scaffold via intramolecular Rh(II) carbene trapping. Tetrahedron Lett. 2021, 85, 153467
  8. Nayebzadeh, B.; Amiri, K.; Khosravi, H.; Mirzaei, S.; Rominger, F.; Dar’in, D.; Krasavin, M.; Bijanzadeh, H. R.; Balalaie, S. Synthesis of Spiro[chromene-imidazo[1,2-a]pyridin]-3'-imines via 6-exo-dig Cyclization Reaction. J. Org. Chem. 2021, 86, 13693-13701
  9. Inyutina, A.; Kantin, G.; Dar´in, D.; Krasavin, M. Diastereoselective Formal [5+2] Cycloaddition of Diazo Arylidene Succinimides-Derived Rhodium Carbenes and Aldehydes: A Route to 2-Benzoxepines. J. Org. Chem. 2021, 86, 13673-13683
  10. Bubyrev, A.; Adamchik, M.; Dar´in, D.; Kantin, G.; Krasavin, M. Metal-Free Three-Component Synthesis of 1,2,3-Triazoline-4-Sulfonamides. J. Org. Chem. 2021, 86, 13454-13464
  11. Safrygin, A.; Zhmurov, P.; Dar'in, D.; Silonov, S.; Kasatkina, M.; Zonis, Y.; Gureev, M.; Krasavin, M. 1-Oxo-3,4-dihydroisoquinoline-4-carboxamides as novel druglike inhibitors of poly(ADP-ribose) polymerase (PARP) with favorable ADME characteristics. J. Enzyme Inhib. Med. Chem. 2021, 36, 1968-1983
  12. Safrygin, A.; Zhmurov, P.; Dar'in, D.; Silonov, S.; Kasatkina, M.; Zonis, Y.; Gureev, M.; Krasavin, M. Three-component Castagnoli-Cushman reaction with ammonium acetate delivers 2-unsubstituted isoquinol-1-ones as potent inhibitors of poly(ADP-ribose) polymerase (PARP). J. Enzyme Inhib. Med. Chem. 2021, 36, 1916-1921
  13. Pilipenko, I.; Korzhikov-Vlakh, V.; Valtari, A.; Anufrikov, Y.; Kalinin, S.; Ruponen, M.; Krasavin, M.; Urtti, A.; Tennikova, T. Mucoadhesive properties of nanogels based on stimuli-sensitive glycosaminoglycan-graft-pNIPAAm copolymers. Int. J. Biol. Macromol. 2021, 186, 8644-872
  14. Solovyev, I.; Dar'in, D.; Krasavin, M. Novel 3,4-dihydro-1,4-oxazine (dehydromorpholine) sulfonamides and sulfones conveniently accessed from suitable alpha-diazoketones via O—H carbene insertion – Cyclization sequence. Tetrahedron Lett. 2021, 78, 153269
  15. Lukin, A.; Bakholdina, A.; Chudinov, M.; Onopchenko, O.; Zhuravel, E.; Zozulya, S.; Gureev, M.; Krasavin, M. Strained contacts with the cell membrane may influence ligand affinity to G protein coupled receptors: a case of free fatty acid receptor 1 agonists. J. Enzyme Inhib. Med. Chem. 2021, 36, 1651-1658
  16. Krasavin, M.; Zhukovsky, D.; Solovyev, I.; Barkhatova, D.; Dar’in, I.; Frank, D.; Martinelli, G.; Weizel, L.; Proschak, A.; Rotter, M.; Kramer, J. S.; Brunst, S.; Wichelhaus, T. A.; Proschak, E.* RhII-Catalyzed De-symmetrization of Ethane-1,2-dithiol and Propane-1,3-dithiol Yields Metallo-β-lactamase Inhibitors, ChemMedChem 2021, 16, 3410-3417. Nominated VERY IMPORTANT PAPER.
  17. Guranova, N.; Dar'in, D.; Kantin, G.; Krasavin, M. Oxonium ylides generated from 1,4-disubstituted α-diazo glutaconimides: a rich source of diverse oxygen heterocyclic frameworks. Eur. J. Org. Chem. 2021, 3411-3420
  18. Dar'in, D.; Kantin, G.; Kalinin, S.; Sharonova, T.; Bunev, A.; Ostapenko, G. I.; Nocentini, A.; Sharoyko, V.; Supuran, C. T.; Krasavin, M. Investigation of 3-sulfamoyl coumarins against cancer-related IX and XII isoforms of human carbonic anhydrase as well as cancer cells leads to the discovery of 2-oxo-2H-benzo[h]chromene-3-sulfonamide – a new caspase-activating proapoptotic agent. Eur. J. Med. Chem. 2021, 222, 113589
  19. Inyutina, A.; Dar'in, D.; Kantin, G.; Krasavin, M. Tricyclic 2-Benzazepines Obtained via an Unexpected Cyclization Involving Nitrilium Ylides. Org. Biomol. Chem. 2021, 19, 5068-5071
  20. Supuran, C. T.; Nocentini, A.; Yakubova, E.; Savchuk, N.; Kalinin, S.; Krasavin, M. Biochemical profiling of anti-HIV prodrug Elsulfavirine (Elpida®) and its active form VM1500A against a panel of twelve human carbonic anhydrase isoforms. J. Enzyme Inhib. Med. Chem. 2021, 36, 1056-1060
  21. Budeev, A.; Kantin, G.; Dar'in, D.; Krasavin, M. Diazocarbonyl and Related Compounds in the Synthesis of Azoles. Molecules 2021, 26, 2530
  22. Dar'in, D.; Kantin, G.; Chupakhin, E.; Sharoyko, V.; Krasavin, M. Natural-like Spirocyclic Δα,β-Butenolides Obtained from Diazo Homophthalimides. Chem. Eur. J. 2021, 27, 8221-8227
  23. Sapegin, A. V.; Peshkov, A. A.; Kanov, E. V.; Gainetdinov, R. R.; Duszyńska, B.; Bojarski, A. J.; Krasavin, M. Novel medium-sized di(het)areno-fused 1,4,7-(oxa)thiadiazecines as probes for aminergic receptors. Mendeleev Commun. 2021, 31, 501-503
  24. Guranova, N.; Golubev, P.; Bakulina, O.; Dar'in, D.; Kantin, G.; Krasavin, M. Unexpected formal [4+2]-cycloaddition of chalcone imines and homophthalic anhydrides: preparation of dihydropyridin-2(1H)-ones. Org. Biomol. Chem. 2021, 19, 3829-3833
  25. Levashova, E.; Firsov, A.; Bakulina, O.; Peshkov, A.; Kanov, E.; Gainetdinov, R. R.; Krasavin, M. Rare cis-configured 2,4-disubstituted-1-alkylpiperidines synthesized and tested against trace-amine-associated receptor 1 (TAAR1). Mendeleev Commun. 2021, 31, 488-489
  26. Reutskaya, E.; Sapegin, A.; Peintner, S.; Erdélyi, M.; Krasavin, M. Sulfur Oxidation Increases the Rate of HIRE-type [1.4]Thiazepinone Ring Expansion and Influences the Conformation of a Medium-Sized Heterocyclic Scaffold. J. Org. Chem. 2021, 86, 5778-5791
  27. Chupakhin, E.; Krasavin, M. Thioredoxin reductase inhibitors: updated patent review (2017-present). Exp. Opin. Ther. Pat. 2021, 31, 745-758
  28. Kazantsev, A.; Zhukovsky, D.; Bubyrev, A.; Dar'in, D.; Krasavin, M. Fluorination of α-diazo-γ-lactams with the Olah reagent. Tetrahedron Lett. 2021, 69, 152969
  29. Sharonova, T.; Paramonova, P.; Kalinin, S.; Bunev, A.; Gasanov, R. E.; Nocentini, A.; Sharoyko, V.; Tennikova, T. B.; Dar'in, D.; Supuran, C. T.; Krasavin, M. Insertion of Metal Carbenes Into the Anilinic N–H Bond of Unprotected Aminobenzenesulfonamides Delivers Low Nanomolar Inhibitors of Human Carbonic Anhydrase IX and XII isoforms. Eur. J. Med. Chem. 2021, 218, 113352
  30. Kalinin, S.; Vedekhina, T.; Paramonova, P.; Krasavin, M. Antimicrobial activity of 5-membered nitroheteroaromatic compounds beyond nitrofurans and nitroimidazoles: recent progress. Curr. Med. Chem. 2021, 28, 5926-5982
  31. Peshkov, A. A.; Bakulina, O.; Dar'in, D.; Kantin, G.; Bannykh, A.; Peshkov, V. A.; Krasavin, M. Three-component Castagnoli-Cushman reaction of 3-arylglutaconic acid anhydrides, carbonyl compounds and ammonium acetate: a quick and flexible way to assemble polysubstituted NH-δ-lactams. Eur. J. Org. Chem. 2021, 1726–1731. COVER FEATURE
  32. Klochkova, A.; Bubyrev, A.; Dar'in, D. Bakulina, O.*; Krasavin, M.; Sokolov, V. Straightforward Route to γ-Sultams via Novel Tandem SN/Michael Addition. Synthesis 2021, 53, 1795-1804
  33. Budeev, A. V.; Kantin, G. P.; Dar'in, D.; Krasavin, M. Continued exploration of trifunctional alkyl 4-chloro-2-diazo-3-oxobutanoates: streamlined entry into [1,2,3]triazolo[5,1-c][1,4]benzoxazines and [1,2,3]triazolo[5,1-c][1,4]benzoxazepines. Synthesis 2021, 53, 2155-2166
  34. Chupakhin, E. G.; Kantin, G. P.; Dar'in, D. V.; Krasavin, M. Convenient preparation of (E)-3-arylidene-4-diazopyrrolidine-2,5-diones in array format. Mendeleev Commun. 2021, 31, 36-38
  35. Chupakhin, E.; Gecht, M.; Ivanov, A.; Kantin, G.; Dar'in, D.; Krasavin, M. (E)-3-Arylidene-4-diazopyrrolidine-2,5-diones: preparation and use in RhII-catalyzed X–H insertion reactions towards novel, medicinally important Michael acceptors. Synthesis 2021, 53, 1292-1300
  36. Solovyev, I.; Eremeyeva, M.; Zhukovsky, D.; Dar'in, D.; Krasavin, M. Cyclic diazo compounds in the construction of spirocyclic scaffolds. Tetrahedron Lett. 2021, 62, 152671
  37. Burianova, V.; Kalinin, S.; Krasavin, M.; Supuran, C. T. Radiotracers for positron emission tomography (PET) targeting tumour-associated carbonic anhydrase isoforms. Eur. J. Med. Chem. 2021, 213, 113046
  38. Bubyrev, A.; Kantin, G.; Dar'in, D.; Krasavin, M. CH-Diazomethane sulfonamides generated in situ for intramolecular [3+2] cycloaddition of alkynes: an entry into novel pyrazole-fused five-membered sultams. Synthesis 2021, 53, 1434-1442 (Featured Article)
  39. Hiesinger, K.; Dar'in, D.; Proschak, E.; Krasavin, M. Spirocyclic Scaffolds in Medicinal Chemistry. J. Med. Chem. 2021, 64, 150–183
  40. Guranova, N.; Kantin, G.; Dar'in, D.; Krasavin, M. Diazo glutaconimides: an unexplored type of heterocyclic α-diazocarbonyl compounds conveniently evolved into pyridine-2,6(1H,3H)-diones and oxazolo[5,4-b]pyridin-5(4H)-ones. Eur. J. Org. Chem. 2021, 623-631
  41. Lukin, A.; Bakholdina, A.; Zhurilo, N.; Onopchenko, O.; Zhuravel, E.; Zozulya, S.; Gureev, M.; Safrygin, A.; Krasavin, M. Exploration of nitrogen heterocyclic periphery around the core of advanced FFA1 agonist fasiglifam (TAK-875). Arch. Pharm. 2021, 354, 2000275

2020

  1. Dar'in, D.; Kantin, G.; Bakulina, O.; Inyutina, A.; Chupakhin, E.; Krasavin, M. Spirocyclizations involving oxonium ylides derived from cyclic α-diazocarbonyl compounds: an entry into 6-oxa-2-azaspiro[4.5]decane scaffold. J. Org. Chem. 2020, 85, 15586-15599
  2. Rashevskii, A.; Bakulina, O.; Novikov, M. S.; Dar'in, D.; Krasavin, M. When periphery matters: enhanced reactivity of 8-oxa-1,4-dithiaspiro[4.5]decane-7,9-dione and 9-oxa-1,5-dithiaspiro[5.5]undecane-8,10-dione in the Castagnoli-Cushman reaction with imines. Tetrahedron Lett. 2020, 61, 152658
  3. Chuprun, S.; Dar'in, D.; Rogacheva, E.; Kraeva, L.; Levin, O.; Manicheva, O.; Dogonadze, M.; Vinogradova, T.; Bakulina, O.; Krasavin, M. Mutually isomeric 2- and 4-(3-nitro-1,2,4-triazol-1-yl)pyrimidines inspired by an antimycobacterial screening hit: synthesis and biological activity against the ESKAPE panel of pathogens. Antibiotics 2020, 9, 666
  4. Jovanović, M.; Dragoj, M.; Zhukovsky, D.; Dar'in, D.; Krasavin, M.; Pešić, M.; Podolski-Renic, A. Novel TrxR1 inhibitors show potential for glioma treatment by suppressing the invasion and sensitizing glioma cells to chemotherapy.Front. Mol. Biosci. 2020, 7, 586146
  5. Lavit, K.; Reutskaya, E.; Grintsevich, S.; Sapegin, A.; Krasavin, M. Zooming in on the hydrated imidazoline ring expansion: factors influencing the rate of N→N′ aroyl migration in N-aroyl-N-(hetero)aryl ethylenediamines. Tetrahedron Lett. 2020, accepted 27.08.2020
  6. Safrygin, A.; Dar'in, D.; Bakulina, O.; Krasavin, M. Synthesis of spirocyclic tetrahydroisoquinolines (spiro-THIQs) via the Castagnoli-Cushman reaction. Tetrahedron Letters 2020, accepted 25.08.2020
  7. Solovyev, I. V.; Zhukovsky, D. D.; Dar'in, D. V.; Krasavin, M. Yu. N-Alkylation of nitrogen heterocycles with α-diazocarbonyl compounds. Chem. Heterocycl. Comp. 2020, 56, 809-813
  8. Levashova, E. Yu.; Zhukovsky, D. D.; Dar'in, D. V.; Krasavin, M. Yu. Synthesis of pyrazoles from α-diazo-β-ketosulfones and α-diazo-β-ketophosphonates Chem. Heterocycl. Comp. 2020, 56, 806-808
  9. Krasavin, M.; Kalinin, S.; Sharonova, T.; Supuran, C. T. Inhibitory activity against carbonic anhydrase IX and XII as a candidate selection criterion in the development of new anticancer agents. J. Enzyme Inhib. Med. Chem. 2020, 35, 1555-1561
  10. Burianova, V.; Dar'in, D.; Krasavin, M. Direct conversion of diazo compounds to fluoro derivatives. Tetrahedron Lett. 2020, 61, 152255 (Invited Digest Article)
  11. Golubev, P.; Guranova, N.; Krasavin, M. 1,3,5-Triazinanes as formaldimine surrogates in the Ugi reaction. Eur. J. Org. Chem. 2020, 4517-4520
  12. Dmitriev, V.; Vedekhina, T.; Sapegin, A.; Krasavin, M. Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines via Two Tandem SNAr Events. Part 3 – (Hetero)arene-fused benzo[f]imidazo[1,2-d][1,4]oxazepines. ChemistrySelect 2020, 5, 7873-7879
  13. Grintsevich, S.; Sapegin, A.; Reutskaya, E.; Peintner, S.; Erdélyi, M.; Krasavin, M. An alternative approach to the hydrated imidazoline ring expansion (HIRE) of diarene-fused [1.4]oxazepines. Eur. J. Org. Chem., accepted 25.06.2020
  14. Inyutina, A.; Chupakhin, E.; Dar'in, D.; Krasavin, M. A novel approach to substituted α-carbamoyl phosphonates — useful reagents for the Horner-Wadsworth-Emmons olefination. Synlett 2020, accepted 16.05.2020
  15. Synofzik, J.; Bakulina, O.; Balabas, O.; Dar'in, D.; Krasavin, M. Catalyst-free synthesis of diastereomerically pure 3-sulfonylazetidin-2-ones via the microwave-assisted tandem Wolff rearrangement–Staudinger cycloaddition. Synthesis 2020, accepted 04.06.2020
  16. Levashova, E.; Bakulina, O.; Dar'in, D.; Bubyrev, A.; Krasavin, M. From rare reagents to rare products: regiospecific silver-catalyzed [3+2] cycloaddition of aryl-, alkyl- and aminosulfonyl diazomethanes with arenediazonium tosylates. Eur. J. Org. Chem. 2020, accepted 04.06.2020
  17. Synofzik, J.; Bakuina, O.; Dar'in, D.; Kantin, G.; Krasavin, M. Dialkyl diazomalonates in transition-metal-free, thermally promoted, diastereoselective Wolff β-lactam synthesis. Synlett 2020, 31, 1273-1276
  18. Kryukova, M. A.; Sapegin, A. V.; Novikov, A. S.; Krasavin, M.; Ivanov, D. M. New Crystal Forms for Biologically Active Compounds. Part 2: Anastrozole as N-substituted 1,2,4-Triazole in Halogen Bonding and Lp-π Interactions with 1,4-Diiodotetrafluorobenzene. Crystals 2020, 10, 371
  19. Bubyrev, A.; Dar'in, D.; Kantin, G.; Krasavin, M. Synthetic studies towards CH-diazomethane sulfonamides: a novel type of diazo reagents. Eur. J. Org. Chem. 2020, 4112-4115. VERY IMPORTANT PAPER
  20. Firsov, A.; Bakulina, O.; Dar'in, D.; Guranova, N.; Krasavin, M. Further Insight into the Castagnoli–Cushman-type Synthesis of 1,4,6-Trisubstituted 1,6-Dihydropyridin-2-(3H)-ones from 3-Arylglutaconic Acid Anhydrides. J. Org. Chem. 2020, 85, 6822-6829
  21. Karchuganova, E.; Bakulina, O.; Dar'in, D.; Krasavin, M. Two annulated azaheterocyclic cores readily available from a single tetrahydroisoquinolonic Castagnoli-Cushman precursor. Molecules 2020, 25, 2049
  22. Chizhova, M. E.; Dar'in, D. V.; Krasavin, M. The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents. Mendeleev. Commun. 2020, 30, 496-497
  23. Bakholdina, A.; Lukin, A.; Bakulina, O.; Guranova, N.; Krasavin, M. Dual use of propargylamine building blocks in the construction of polyheterocyclic scaffolds. Tetrahedron Lett. 2020, 61, 151970
  24. Kuranov, S. O.; Luzina, O. A.; Onopchenko, O.; Pishel, I.; Zozulya, S.; Gureev, M.; Salakhutdinov, N. F.; Krasavin, M. Exploring bulky natural and natural-like periphery in the design of p-(benzyloxy)phenylpropionic acid agonists of free fatty acid receptor 1 (GPR40). Bioorg. Chem. 2020, 99, 103830
  25. Dar'in, D.; Kantin, G.; Bakulina, O.; Krasavin, M. Facile one-pot access to α-diazo-β-ketosulfones from sulfonyl chlorides and α-haloketones. Synthesis 2020, 52, 2259-2266
  26. Safrygin, A.; Bakulina, O.; Dar'in, D.; Krasavin, M. Three-component reaction of homophthalic anhydride with carbonyl compounds and ammonium acetate: new developments. Synthesis 2020, 52, 2190-2195
  27. Eremeyeva, M.; Zhukovsky, D.; Dar'in, D.; Krasavin, M. Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in RhII-catalyzed X-H insertion reactions. Beistein J. Org. Chem. 2020, 16б 607-610
  28. Shevalev, R. M.; Zhmurov, P. A.; Dar'in, D. V.; Krasavin, M. Taking diazo transfer to water: α-diazo carbonyl compounds from in situ generated mesyl azide. Mendeleev Commun. 2020, 30, 372-373
  29. Eremeyeva, M.; Zhukovsky, D.; Dar’in, D.; Krasavin. M. The use of α-diazo-γ-butyrolactams in the Büchner-Curtius-Schlotterbeck reaction of cyclic ketones opens new entry to spirocyclic pyrrolidones. Synlett 2020, 31, 982–986
  30. Zhmurov, P. A.; Dar’in, D. V.; Bakulina, O. Yu.; Krasavin, M. One-pot preparation of methyl α-diazo-β-oxopropionates involving an aqueous ‘Sulfonyl-Azide-Free’ (SAFE) diazo transfer step. Mendeleev Commun. 2020, 30, 311-312
  31. Krasavin, M.; Sharonova, T.; Sharoyko, V.; Zhukovsky, D.; Kalinin, S.; Žalubovskis, R.; Tennikova, T.; Supuran, C. T. Combining carbonic anhydrase and thioredoxin reductase inhibitory motifs within a single molecule dramatically increases its cytotoxicity. J. Enzyme Inhib. Med. Chem. 2020, 35, 665-671
  32. Zhukovsky, D.; Dar'in, D.; Krasavin, M. tert-Butyl 3-diazo-2-oxopyrrolidine-1-carboxylate – a new reagent for introduction of the privileged 2-oxopyrrolidin-3-yl motif via RhII-catalyzed X-H insertion reactions. Eur. J. Org. Chem. 2020, 2013-2018
  33. Jovanović, M.; Zhukovsky, D.; Podolski-Renić, A.; Žalubovskis, R.; Dar’in, D.; Sharoyko, V.; Tennikova, T.; Pešić, M.; Krasavin, M. Further exploration of DVD-445 as a lead thioredoxin reductase (TrxR) inhibitor for cancer therapy: optimization of potency and evaluation of anticancer potential. Eur. J. Med. Chem. 2020, 191, 112119
  34. Chupakhin, E.; Babich, O.; Prosekov, A.; Asyakina, L.; Gureev, M.; Krasavin, M. Plants of the Russian Federation Pharmacopeia: an unexhausted natural products research opportunity? Nat. Prod. Res. 2020, accepted 25.01.2020
  35. Pustenko, A.; Nocentini, A.; Balašova, A.; Krasavin, M.; Žalubovskis, R.; Supuran, C. T. 7-Acylamino-3H-1,2-benzoxathiepine 2,2-dioxides as new isoform-selective carbonic anhydrase IX and XII inhibitors. J. Enzyme Inhib. Med. Chem. 2020, 35, 650-656
  36. Bolotin , D. S.; Soldatova, N. S.; Demakova, M. Ya.; Novikov A. S.; Ivanov, D. M.; Aliyarova, I. S.; Sapegin, Krasavin, M. Pentacoordinated Silver(I) Complex Featuring 8-Phenylquinoline Ligands: Interplay of Coordination Bonds, Semicoordination, and Stacking Interactions. Inorg. Chim. Acta 2020, 504, 119453
  37. Dar'in, D.; Khoroshilova, O.; Kantin, G.; Krasavin, M. Realizing the trifunctional potential of alkyl 4-chloro-2-diazo-3-oxobutanoates: convenient assembly of 6,7-dihydro-4H-[1,2,3]triazolo[5,1-c][1,4]thiazine core. Synthesis 2020, 52, 1266-1272
  38. Krasavin, M.; Žalubovskis, R.; Grandāne, A.; Domračeva, I.; Zhmurov, P.; Supuran, C. T. Sulfocoumarins as dual inhibitors of human carbonic anhydrase isoforms IX/XII and of human thioredoxin reductase. J. Enzyme Inhib. Med. Chem. 2020, 35, 506-510
  39. Chuprun, S.; Dar'in, D.; Kantin, G.; Zhmurov, P.; Krasavin, M. α-Diazoacetamides in Sc(OTf)3-catalyzed Tiffeneau-Demjanov ring expansion: application towards the synthesis of rare bicyclic pyrazoles. Synlett 2020, 31, 373-377
  40. Krasavin, M.; Kalinin, S.; Zozulya, S.; Griniukova, A.; Borysko, P.; Angeli, A.; Supuran, C. T. Further validation of Strecker-type α-aminonitriles as a new class of potent human carbonic anhydrase II inhibitors: hit expansion within the public domain using differential scanning fluorimetry leads to chemotype refinement. J. Enzyme Inhib. Med. Chem. 2020, 35, 165-171
  41. Pustenko, A.; Nocentini, A.; Balašova, A.; Krasavin, M.; Žalubovskis, R.; Supuran, C. T. Aryl derivatives of 3H-1,2-benzoxathiepine 2,2-dioxide as carbonic anhydrase inhibitors. J. Enzyme Inhib. Med. Chem. 2020, 35, 245-254
  42. Krasavin, M.; Kalinin, S.; Zozulya, S.; Gryniukova, A.; Borysko, P.; Angeli, A.; Supuran, C. T. Screening of benzenesulfonamide in combination with chemically diverse fragments against carbonic anhydrase by differential scanning fluorimetry. J. Enzyme Inhib. Med. Chem. 2020, 35, 306-310
  43. Vedekhina, T.; Lukin, A.; Krasavin, M. Unexpected outcome of the Zn(OTf)2-catalyzed arylhydrazination of alkanoyl propargylamines: rapid entry into 1-(arylamino)imidazoles. Tetrahedron Lett. 2020, 61, 161365
  44. Vedekhina, T.; Lukin, A.; Rogacheva, E.; Kraeva, L.; Krasavin, M. Zn(OTf)2-catalyzed arenehydrazination of protected propargylamines leading to 3-amidoindoles. Tetrahedron Lett. 2020, 61, 151430

2019

  1. Chupakhin, E.; Babich, O.; Prosekov, A.; Asyakina, L.; Krasavin, M. Spirocyclic motifs in natural products. Molecules 2019, 24, 4165
  2. Solovyov, I.; Dar'in, D.; Krasavin, M. Convenient approach to 2-substituted (thio)morpholin-3-ones from α-diazoacetates via X-H carbene insertion — lactamization sequence. Eur. J. Org. Chem. 2019, 7432-7438
  3. Gecht, M.; Kantin, G.; Dar'in, D.; Krasavin, M. A novel approach to biologically relevant oxazolo[5,4-d]pyrimidine-5,7-diones via readily available diazobarbituric acid derivatives. Tetrahedron Lett. 2019, 60, 151120
  4. Kalinin, S.; Valtari, A.; Ruponen, M.;Toropainen, E.; Kovalenko, A.; Nocentini, A.; Gureev, M.; Dar’in, D.; Urtti, A.; Supuran, C. T.; Krasavin, M. Highly Hydrophilic 1,3-Oxazol-5-yl Benzenesulfonamide Inhibitors of Carbonic Anhydrase II for Reduction of Glaucoma-Related Intraocular Pressure. Bioorg. Med. Chem. 2019, 27, 115086
  5. Kalinin, S.; Nocentini, A.; Kovalenko, A.; Sharoyko, V.; Bonardi, A.; Angeli, A.; Gratteri, P.; Tennikova, T. B.; Supuran, C. T.; Krasavin, M. From Random to Rational: A Discovery Approach to Selective Subnanomolar Inhibitors of Human Carbonic Anhydrase IV Based on the Castagnoli-Cushman Multicomponent Reaction. Eur. J. Med. Chem. 2019, 182, 111642
  6. Synofzik, J.; Dar’in, D.; Novikov, M. S.; Kantin, G.; Bakulina, O.; Krasavin, M. α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis. J. Org. Chem. 2019, 84, 12101-12110
  7. Krasavin, M. Yu.; Gureev, M. A.; Garabadzhiu, A. V.; Pashkin, A. Yu.; Zhukov, A. S.; Khairutdinov, V. R.; Samtsov, A. V.; Shvets, V. I. Inhibition of Neutrophil Elastase and Cathepsin G as a New Approach to the Treatment of Psoriasis: From Fundamental Biology to Development of New Target-Specific Drugs. Doklady Biochem. Biophys. 2019, 487, 272-276
  8. Usmanova, L.; Dar'in, D.; Krasavin, M. Downstream modification of piperazin-2-ones obtained by the Castagnoli-Cushman reaction leads to a novel version of the medicinally relevant 1,2,5-benzothiadiazepin-4-one-1,1-dioxide scaffold. Tetrahedron Lett. 2019, 60, 151003
  9. Dar'in, D.; Kantin, G.; Krasavin, M. Practical Application of the Aqueous ‘Sulfonyl-Azide-Free’ (SAFE) Diazo Transfer Protocol to Less α-C-H Acidic Ketones and Esters. Synthesis 2019, 51, 4284-4290
  10. Jovanović, M.; Zhukovsky, D.; Podolski-Renić, A.; Domračeva, I.; Žalubovskis, R.; Senćanski, M.; Glišić, S.; Sharoyko, V.; Tennikova, T.; Dar’in, D.; Pešić, M.; Krasavin, M. Novel electrophilic amides amenable by the Ugi reaction perturb thioredoxin system via thioredoxin reductase 1 (TrxR1) inhibition: identification of DVD-445 as a new lead compound for anticancer therapy. Eur. J. Med. Chem. 2019, 181, 111580
  11. Barkhatova, D.; Zhukovski, D.; Dar'in, D.; Krasavin, M. Employing α-diazocarbonyl compound chemistry in the assembly of medicinally important aryl(alkyl)thiolactam scaffold. Eur. J. Org. Chem. 2019, 5798-5800
  12. Chuprun, S.; Dar'in, D.; Kantin, G.; Krasavin, M. [2+3]-Cycloaddition of α-Diazocarbonyl Compounds with Arenediazonium Salts Catalyzed by Silver Nitrate Delivers 2,5-Disubstituted Tetrazoles. Synthesis 2019, 51, 3998-4005
  13. Safrygin, A.; Dar'in, D.; Kantin, G.; Krasavin, M. α‐Diazo‐β‐oxosulfones as Partners in the Wolff 1,2,3‐Triazole Synthesis and the Wolff Rearrangement in the Presence of Aromatic Amines. Eur. J. Org. Chem. 2019, 4721–4724
  14. Sapegin, A.; Krasavin, M. One-pot Conversion of Aldehydes and Aryl Halides to Disubstituted Alkynes via Tandem Seyferth-Gilbert Homologation/Copper-Free Sonogashira Coupling. J. Org. Chem. 2019, 84, 8788-8795
  15. Golushko, A.; Dar'in, D.; Kantin, G.; Guranova, N.; Vasilyev, A. V.; Krasavin, M. Medicinally Relevant Modification of the Isoquinoline-1,3-dione Scaffold via Metal-Free Arylation and Fluorination of Diazo Homophthalimides in Brønsted Acids. Synthesis 2019, 51, 3815-3824
  16. Shershnev, I.; Dar'in, D.; Chuprun, S.; Kantin, G.; Bakulina, O.; Krasavin, M. The use of α-diazo-γ-butyrolactone in the Büchner-Curtius-Schlotterbeck reaction of cyclic ketones: a facile entry into spirocyclic scaffolds. Tetrahedron Lett. 2019, 60. 1800-1802
  17. Zhukovsky, D.; Dar'in, D.; Krasavin, M. Rh2(esp)2-Catalysed Coupling of α-Diazo-γ-butyrolactams with Aromatic Amines. Eur. J. Org. Chem. 2019, 4377-4383
  18. Golubev, P.; Pankova, A.; Krasavin, M. “Isocyanide-less” Ugi/Intramolecular Diels-Alder reaction of 5-hydroxymethylfurfural. Tetrahedron Lett. 2019, 60б 1578-1581
  19. Guranova, N. I.; Dar'in, D.; Kantin, G.; Novikov, A. D.; Bakulina, O.; Krasavin, M. Fused vs. spiro: kinetic, not thermodynamic preference may direct the reaction of alpha-carbonyl oxonium ylides. Tetrahedron Lett. 2019, 60, 1582-1586
  20. Firsov, A.; Sapegin, A.; Krasavin, M. Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines via Two Tandem SNAr Events. Part 2 — The Use of o-[N-(Hetero)aryl]aminomethyl phenols. Eur. J. Org. Chem. 2019, 5242-5246
  21. Bakulina, O.; Rashevskii, A.; Dar'in, D.; Halder, S.; Khagar, P.; Krasavin, M. Modular assembly of tunable fluorescent chemosensors selective for Pb2+ and Cu2+ metal ions via the multicomponent Castagnoli-Cushman reaction. ChemistrySelect 2019, 4, 6066-6073
  22. Lukin, A.; Bakholdina, A.; Kryukova, A.; Sapegin, A.; Krasavin, M. A three-component, Zn(OTf)2-mediated entry into trisubstituted 2-aminoimidazoles. Beilstein J. Org. Chem. 2019, 15, 1061-1064
  23. Levels, M. J.; Fehres, C. M.; van Baarsen, L. G. M.; van Uden, N. O. P.; Germar, K.; O'Toole, T. G.; Blijdorp, I. C. J.; Semmelink, J. F.; Doorenspleet, M. E.; Bakker, A. Q.; Krasavin, M.; Tomilin, A.; Brouard, S.; Spits, H.; Baeten, D. L. P.; Yeremenko, N. G. BOB.1 controls memory B-cell fate in the germinal center reaction. J. Autoimmun. 2019, 101, 131-144
  24. Dar'in, D.; Kantin, G.; Krasavin, M. A ‘Sulfonyl-Azide-Free’ (SAFE) Aqueous-Phase Diazo Transfer Reaction for Parallel and Diversity-Oriented Synthesis. Chem. Commun. 2019, 55, 5239-5242
  25. Sapegin, A.; Krasavin, M. Convenient Assembly of Privileged (Hetero)Arene-Fused Benzo[1.4]oxazepines via Two Tandem SNAr Events. Part 1 — On the Importance of the Intermittent Smiles Rearrangement. Eur. J. Org. Chem. 2019, 5234-5241
  26. Shetnev, A.; Baykov, S.; Kalinin, S.; Belova, A.; Sharoyko, V.; Rozhkov, A.; Zelenkov, L.; Tarasenko, M.; Sadykov, E.; Korsakov, M.; Krasavin, M. 1,2,4-Oxadiazole/2-imidazoline hybrids: Multi-target-directed compounds for the treatment of infectious diseases and cancer. Int. J. Mol. Sci. 2019, 20, 1699; doi:10.3390/ijms20071699
  27. Bannykh, A. V.; Bakulina, O. Yu., Dar'in, D. V.; Krasavin, M. Yu. Hydroxylamine as an ammonia equivalent: access to NH-tetrahydroisoquinolonic derivatives from aldoximes by the Castagnoli–Cushman reaction followed by reduction. Mendeleev Commun. 2019, 29, 337-338
  28. Zhukovsky, D.; Dar'in, D.; Kantin, G.; Krasavin, M. Synthetic exploration of α-diazo γ-butyrolactams. Eur. J. Org. Chem. 2019, 2397-2400
  29. Chupakhin, E.; Bakulina, O.; Dar'in, D.; Krasavin, M. 1,1'-Carbonyldiimidazole as a novel cyclodehydrating agent for the Castagnoli−Cushman reaction of dicarboxylic acids and imines. Mendeleev Commun. 2019, 29, 292-293
  30. Bolotin, S. S.; Korzhikov-Vlakh, V.; Sinitsyna, E.; Yunusova, S. N.; Suslonov, V. V.; Shetnev, A.; Osipyan, A.; Krasavin, M.; Kukushkin, V. Biocompatible Zinc(II) 8-(Dihydroimidazolyl)quinoline Complex and its Catalytic Application for Synthesis of Poly(L,L-lactide). J. Catal. 2019, 372, 362-369
  31. Guranova, N.; Dar'in, D.; Kantin, G.; Novikov, A.; Bakulina, O.; Krasavin, M. Rh(II)-Catalyzed Spirocyclization of α-Diazo Homophthalimides with Cyclic Ethers. J. Org. Chem. 2019, 84, 4534-4542
  32. Chupakhin, E.; Bakulina, O.; Dar'in, D.; Krasavin, M. Facile access to Fe(III)-complexing cyclic hydroxamic acids in a three-component format. Molecules 2019, 24, 864
  33. Firsov, A.; Chupakhin, E.; Dar'in, D.; Bakulina, O.; Krasavin, M. Three-Component Castagnoli-Cushman Reaction of 3-Arylglutaconic Acids with Aromatic Aldehydes and Amines Delivers Rare 4,6-Diaryl 1,6-Dihydropyridine-2(3H)-ones. Org. Lett. 2019, 21, 1637-1640
  34. Krasavin, M.; Shetnev, A.; Baykov, S.; Kalinin, S.; Nocentini, A.; Sharoyko, V.; Poli, G.; Tuccinardi, T.; Korsakov, M.; Tennikova, T. B.; Supuran, C. T. Pyridazinone-substituted benzenesulfonamides display potent inhibition of membrane-bound human carbonic anhydrase IX and promising antiproliferative activity against cancer cell lines. Eur. J. Med. Chem. 2019, 168, 301-314
  35. Safrygin, A.; Dar'in, D.; Lukin, A.; Bakholdina, A.; Sapegin, A.; Krasavin, M. Zn(OTf)2-catalyzed, microwave-promoted synthesis of 2-substituted 5-methyloxazoles from propargylic amides. Tetrahedron Lett. 2019, 60, 777-779
  36. Dar'in, D.; Kantin, G.; Bakulina, O.; Zalubovskis, R.; Krasavin, M. Flexible entry into 3-arylpent-2-enedioic acids via Heck-Matsuda arylation of dimethyl glutaconate with arenediazonium tosylates. Synthesis 2019, 51, 2230-2236
  37. Dubovtsev, A. Yu.; Dar'in, D. V.; Krasavin, M.; Kukushkin, V. Yu. Gold-catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles. Eur. J. Org. Chem. 2019, 1856
  38. Kryukova, M.; Sapegin, A.; Novikov, A.; Krasavin, M.; Ivanov. D. New Crystal Forms For Biologically Active Compounds. Part 1: Non-covalent Interactions in Adducts of Nevirapine with XB Donors. Crystals 2019, 9, 71
  39. Li-Zhulanov, N. S.; Il’ina, I. V.; Chicca, A.; Schenker, P.; Patrusheva, O. S.; Nazimova, E. V.; Korchagina, D. V.; Krasavin, M.; Volcho, K. P.; Salakhutdinov, N. F. Effect of chiral polyhydrochromenes on cannabinoid system. Med. Chem. Res. 2019, 28, 450-464
  40. Bakulina, O.; Bannykh, A.; Jovanović, M.; Domračeva, I.; Podolski-Renić, A.; Žalubovskis, R.; Pešić, M.; Dar’in, D.; Krasavin, M. Design, synthesis and biological evaluation of novel derivatives of dithiodiglycolic acid prepared via oxidative coupling of thiols. J. Enzyme Inhib. Med. Chem. 2019, 34, 665-671
  41. Krasavin, M.; Lukin, A.; Vedekhina, T.; Manicheva, O.; Dogonadze, M.; Vinogradova, T.; Zabolotnykh, N.; Rogacheva, E.; Kraeva, L.; Sharoyko, V.; Tennikova, T. B.; Dar’in, D.; Sokolovich, E. Attachment of a 5-nitrofuroyl moiety to spirocyclic piperidines produces non-toxic nitrofurans that are efficacious in vitro against multidrug-resistant Mycobacterium tuberculosis. Eur. J. Med. Chem. 2019. 166, 125-135
  42. Iakovenko, R.; Chicca, A.; Nieri, D.; Reynoso-Moreno, I.; Gertsch, J.; Krasavin, M.; Vasilyev, A. Synthesis of various arylated trifluoromethyl substituted indanes and indenes, and study of their biological activity. Tetrahedron 2019, 75, 624-632
  43. Krasavin, M.; Shetnev, A.; Sharonova, T.; Baykov, S.; Kalinin, S.; Nocentini, A.; Sharoyko, V.; Poli, G.; Tuccinardi, T.; Presnukhina, S.; Tennikova, T. B.; Supuran, C. T. Continued exploration of 1,2,4-oxadiazole periphery for carbonic anhydrase-targeting primary arene sulfonamides: discovery of subnanomolar inhibitors of membrane-bound hCA IX isoform that selectively kill cancer cells in hypoxic environment. Eur. J. Med. Chem. 2019, 164, 92-105
  44. Reutskaya, E.; Osipyan, A.; Sapegin, A.; Novikov, A.; Krasavin, M. Re-thinking Hydrolytic Imidazoline Ring Expansion: A Common Approach to the Preparation of Medium-Sized Rings via Side Chain Insertion into [1.4]Oxa- and [1.4]Thiazepinone Scaffold. J. Org. Chem. 2019, 84, 1693-1705
  45. Grintsevich, S.; Sapegin, A.; Reutskaya, E.; Krasavin, M. Antiviral drug nevirapine as a template for hydrated imidazoline ring expansion (HIRE): rapid access to the diarene-fused 1,4,7-triazecine ring system. Tetrahedron Lett. 2019, 60, 20-22
  46. Dar'in, D.; Zarubaev, V.; Galochkina, A.; Gureev, M.; Krasavin, M. Non-chelating p-phenylidene-linked bis-imidazoline analogs of known influenza virus endonuclease inhibitors: synthesis and anti-influenza activity. Eur. J. Med. Chem. 2019, 161, 526-532
  47. Kryukova, M. A.; Sapegin, A. V.; Novikov, A. S.; Krasavin, M.; Ivanov, D. M. Non-covalent interactions observed in nevirapinium pentaiodide hydrate which include the rare I4-I-•••O=C halogen bonding. Z. Kristallogr. Cryst. Mater. 2019, 234, 101-108

2018

  1. Chizhova, M.; Khoroshilova, O.; Dar'in, D.; Krasavin, M. Unusually Reactive Cyclic Anhydride Expands the Scope of the Castagnoli-Cushman Reaction. J. Org. Chem. 2018, 83, 12722-12733
  2. Chizhova, M.; Khoroshilova, O.; Dar’in, D.; Krasavin, M. Acetic anhydride to the rescue: facile access to privileged 1,2,3,4-tetrahydropyrazino[1,2-a]indole core via the Castagnoli-Cushman reaction. Tetrahedron Lett. 2018, 59, 3612-3615
  3. Krasavin, M.; Lukin, A.; Vedekhina, T.; Manicheva, O.; Dogonadze, M.; Vinogradova, T.; Zabolotnykh, N.; Rogacheva, E.; Kraeva, L.; Yablonsky, P. Conjugation of a 5-nitrofuran-2-oyl moiety to aminoalkylimidazoles produces non-toxic nitrofurans that are efficacious in vitro and in vivo against multidrug-resistant Mycobacterium tuberculosis. Eur. J. Med. Chem. 2018, 157, 1115-1126
  4. Osipyan, A.; Sapegin, A.; Novikov, A.; Krasavin, M. Rare Medium-Sized Rings Prepared via Hydrolytic Imidazoline Ring Expansion (HIRE). J. Org. Chem. 2018, 83, 9707-9717
  5. Golubev, P.; Krasavin, M. N-Isocyanodialkylamines Generated In Situ for the Joullié-Ugi reaction with Indolenines. Tetrahedron Lett. 2018, 59, 3532-3536
  6. Kantin, G.; Dar'in, D.; Krasavin, M. Rh(II)-catalyzed Cycloaddition of α-Diazo Homophthalimides and Nitriles Delivers Novel Oxazolo[5,4-c]isoquinolin-5(4H)-one Scaffold. Eur. J. Org. Chem. 2018, 4857-4859
  7. Lukin, A.; Kramer, J.; Hartmann, M.; Weizel, L.; Hernandez-Olmos, V.; Falahati, K.; Burghardt, I.; Kalinchenkova, N.; Bagnyukova, D.; Zhurilo, N.; Rautio, J.; Forsberg, M.; Ihalainen, J.; Auriola, S.; Leppänen, J.; Konstantinov, I.; Pogoryelov, D.; Proschak, E.; Dar’in, D.; Krasavin, M. Discovery of Polar Spirocyclic Orally Bioavailable Urea Inhibitors of Soluble Epoxide Hydrolase. Bioorg. Chem. 2018, 80, 655-667
  8. Chuprun, S. S.; Kantin, G.; Krasavin, M. Synthesis and Medicinal Applications of N-Aryl-C-nitroazoles. Mini Rev. Med. Chem. 2018, 18, 1733-1752
  9. Chupakhin, E. G.; Krasavin, M. Yu. Achievements in the synthesis of cyclooctynes for ring strain-promoted [3+2] azide-alkyne cycloaddition. Chem. Heterocycl. Compd. 2018, 54, 483-501
  10. Safrygin, A.; Krivosheyeva, E.; Dar'in, D.; Krasavin, M. Efficient conversion of tertiary propargylamides into imidazoles via hydroamination-cyclization. Synthesis 2018, 50, 3048-3058
  11. Lukin, A.; Kalinchenkova, N.; Vedekhina, T.; Zhurilo, N.; Krasavin, M. Diversity-oriented synthesis of N,N-dimethylamino-substituted azoles employing TBTU. Tetrahedron Lett. 2018, 59, 2732-2735
  12. Chupakhin, E.; Dar'in, D.; Krasavin, M. The Castagnoli-Cushman Reaction in a three-component format. Tetrahedron Letters 2018, 59, 2595-2599
  13. Konovalov, A. I.; Antipin, I. S.; Burilov, V. A.; Madzhidov, T. I.; Kurbangalieva, A. R.; Nemtarev, A. V.; Solovieva, S. E.; Stoikov, I. I.; Mamedov, V. A.; Zakharova, L. Ya.; Gavrilova, E. L.; Sinyashin, O. G.; Balova, I. A.; Vasilyev, A. V.; Zenkevich, I. G.; Krasavin, M. Yu.; Kuznetsov, M. A.; Molchanov, A. P.; Novikov, M. S.; Nikolaev, V. A.; Rodina, L. L.; Khlebnikov, A. F.; Beletskaya, I. P.; Vatsadze, S. Z.; Gromov, S. P.; Zyk, N. V.; Lebedev, A. T.; Lemenovskii, D. A.; Petrosyan, V. S.; Nenaidenko, V. G.; Negrebetskii, V. V.; Baukov, Yu. I.; Shmigol', T. A.; Korlyukov, A. A.; Tikhomirov, A. S.; Shchekotikhin, A. E.; Traven', V. F.; Voskresenskii, L. G.; Zubkov, F. I.; Golubchikov, O. A.; Semeikin, A. S.; Berezin, D. B.; Stuzhin, P. A.; Filimonov, V. D.; Krasnokutskaya, E. A.; Fedorov, A. Yu.; Nyuchev, A. V.; Orlov, V. Yu.; Begunov, R. S.; Rusakov, A. I.; Kolobov, A. V.; Kofanov, E. R.; Fedotova, O. V.; Egorova, A. Yu.; Charushin, V. N.; Chupakhin, O. N.; Klimochkin, Yu. N.; Osyanin, V. A.; Reznikov, A. N.; Fisyuk, A. S.; Sagitullina, G. P.; Aksenov, A. V.; Aksenov, N. A.; Grachev, M. K.; Maslennikova, V. I.; Koroteev, M. P.; Brel', A. K.; Lisina, S. V.; Medvedeva, S. M.; Shikhaliev, Kh. S.; Suboch, G. A.; Tovbis, M. S.; Mironovich, L. M.; Ivanov, S. M.; Kurbatov, S. V.; Kletskii, M. E.; Burov, O. N.; Kobrakov, K. I.; Kuznetsov, D. N. Modern Trends of Organic Chemistry in Russian Universities. Russ. J. Org. Chem. 2018, 54, 157–371
  14. Bakulina, O.; Dar'in, D.; Krasavin, M. Mixed Carboxylic-Sulfonic Anhydride in Reactions with Imines: A Straightforward Route to Water-Soluble Beta-Lactams via a Staudinger-Type Reaction. Org. Biomol. Chem. 2018, 16, 3989-3998
  15. Usmanova, L.; Dar'in, D.; Novikov, M. S.; Gureev, M.; Krasavin, M. Bicyclic Piperazine Mimetics of the Peptide Beta-Turn Assembled via the Castagnoli-Cushman Reaction. J. Org. Chem. 2018, 83, 5859-5868
  16. Krasavin, M.; Gureyev, M. A.; Dar’in, D.; Bakulina, O.; Chizhova, M.; Lepikhina, A.; Novikova, D.; Grigoreva, T.; Ivanov, G.; Zhumagalieva, A.; Garabadzhiu, A. V.; Tribulovich V. G. Design, in silico prioritization and biological profiling of apoptosis-inducing lactams amenable by the Castagnoli-Cushman reaction. Bioorg. Med. Chem. 2018, 26, 2651-2673
  17. Sapegin, A.; Krasavin, M. Efficient Suzuki-Miyaura mono-arylation of symmetrical diiodo(hetero)arenes. Tetrahedron Lett. 2018, 59, 1948-1951
  18. Burianova, V.; Bolotin, D.; Mikherdov, A.; Novikov, A.; Mokolokolo, P.; Roodt, A.; Boyarskiy, V.; Dar'in, D.; Krasavin, M.; Suslonov, V.; Zhdanov, A.; Zhizhin, K.; Kuznetsov, N. Mechanism of Generation of closo-Decaborato Amidrazones. Intramolecular Non-covalent B–H•••π(Ph) Interaction Determines Stabilization of the Configuration around the Amidrazone C=N Bond. New J. Chem. 2018, 42, 8693-8703
  19. Tutov, A.; Bakulina, O.; Dar'in, D.; Krasavin, M. Concise Synthesis of 2-N-Hydroxy-3,4-dihydroisoquinol-2-one: a Bacterial Siderophore and Human 5-Lipooxygenase Inhibitor. Tetrahedron Lett. 2018, 59, 1511-1512
  20. Mikheyev, A.; Kantin, G.; Krasavin, M. Aldazines in the Castagnoli-Cushman reaction. Synthesis 2018, 50, 2076-2086
  21. Sapegin, A.; Krasavin, M. 1,4-Diiodo-2,3,5,6-tetrafluorobenzene (DITFB) in the Synthesis of Polyfluorinated Organic Compounds. J. Fluorine Chem. 2018, 209, 56-64
  22. Bakulina, O.; Chizhova, M.; Dar'in, D.; Krasavin, M. A General Way to Construct Arene-Fused Seven-Membered Nitrogen Heterocycles. Eur. J. Org. Chem. 2018, 362-371
  23. Guranova, N.; Dar'in, D.; Krasavin, M. Facile access to 3-unsubstituted tetrahydroisoquinolonic acids via the Castagnoli-Cushman reaction. Synthesis 2018, 50, 2076-2086
  24. Moreau, E.; Dar'in, D.; Krasavin, M. The first example of azole-fused cyclic anhydride reacting in the Castagnoli-Cushman way. Synlett 2018, 29, 890-893
  25. Sapegin, A.; Kalinin, S.; Angeli, A.; Supuran, C. T.; Krasavin, M. Unprotected primary sulfonamide group facilitates ring-forming cascade en route to polycyclic [1.4]oxazepine-based carbonic anhydrase inhibitors. Bioorg. Chem. 2018, 76, 140-146
  26. Krasavin, M.; Shetnev,A.; Sharonova, T.; Baykov, S.; Tuccinardi, T.; Kalinin, K.; Angeli, A.; Supuran, C. T. Heterocyclic Periphery in the Design of Carbonic Anhydrase Inhibitors: 1,2,4-Oxadiazol-5-yl Benzenesulfonamides as Potent and Selective Inhibitors of Cytosolic hCA II and Membrane-Bound hCA IX Isoforms. Boorg. Chem. 2018, 76, 88-97

2017

  1. Bakulina, O.; Bannykh, A.; Dar’in, D.; Krasavin, M. Iron-Complexing Cyclic Hydroxamic Acid Analogs of Bacterial Siderophores Prepared via the Castagnoli-Cushman Reaction of Unprotected Oximes. Chem. Eur. J. 2017, 23, 17667 – 17673
  2. Lepikhina, A.; Dar'in, D.; Bakulina, O.; Chupakhin, E.; Krasavin, M. Skeletal Diversity in Combinatorial Fashion: A New Format for the Castagnoli-Cushman Reaction. ACS Comb. Sci. 2017, 19, 702-707
  3. Kalinin, S.; Kopylov, S.; Tuccinardi, T.; Sapegin, A.; Dar'in, D.; Angeli, A.; Supuran, C. T.; Krasavin, M. Lucky Switcheroo: Dramatic Potency and Selectivity Improvement of Imidazoline Inhibitors of Human Carbonic Anhydrase VII. ACS Med. Chem. Lett. 2017, 8, 1105−1109
  4. Krasavin, M.; Lukin, A.; Bakholdina, A.; Zhurilo, N.; Onopchenko, O.; Borysko, P.; Zozulya, S.; Moore, D.; Tikhonova, I. G. Continued SAR Exploration of 1,2,4-Thiadiazole-containing Scaffolds in the Design of Free Fatty Acid Receptor 1 (GPR40) agonists. Eur. J. Med. Chem. 2017, 140, 229-238
  5. Galambos, J.; Bielik, A.; Wágner, G.; Domány, G.; Kóti, J.; Béni, Z.; Szigetvári, A.; Sánta, Z.; Orgován, Z.; Bobok, A.; Kiss, b.; Mikó-Bakk, M. L.; Vastag, M.; Sághy, K.; Krasavin, M.; Gál, K.; Greiner, I.; Szombathelyi, Z.; Keserű, G. M. Discovery of 4-amino-3-arylsulfoquinolines, a novel non-acetylenic chemotype of metabotropic glutamate 5 (mGlu5) receptor negative allosteric modulators. Eur. J. Med. Chem. 2017, 133, 240-254
  6. Chizhova, M.; Dar'in, D.; Krasavin, M. Complications in the Castagnoli-Cushman reaction: an unusual course of reaction between cyclic anhydrides and sterically hindered indolenines. Tetrahedron Lett. 2017, 58, 3470-3473
  7. Bakulina, O.; Ivanov, A.; Suslonov, V.; Dar'in, D.; Krasavin, M. A Speedy Route to Sterically Encumbered, Benzene-fused Derivatives of Privileged, Naturally Occurring Hexahydropyrrolo[1,2-b]isoquinoline. Beilstein J. Org. Chem. 2017, 13, 1413-1424
  8. Kantin, G.; Chupakhin, E.; Dar'in, D.; Krasavin, M. Efficient cyclodehydration of dicarboxylic acids with oxalyl chloride. Tetrahedron Lett. 2017, 58, 3160-3163
  9. Krasavin, M.; Korsakov, M.; Ronzhina, O.; Tuccinardi, T.; Kalinin, S.; Tanç, M.; Supuran, C. T. Primary mono- and bis-sulfonamides obtained via regiospecific sulfochlorination of N-arylpyrazoles: inhibition profile against a panel of human carbonic anhydrases. J. Enz. Inhib. Med. Chem. 2017, 32, 920-934
  10. Ferraroni, M.; Luccarini, L.; Masini, E.; Korsakov, M.; Scozzafava, A.; Supuran, C. T.; Krasavin, M. 1,3-Oxazole-based selective picomolar inhibitors of cytosolic human carbonic anhydrase II alleviate ocular hypertension in rabbits: potency is supported by X-ray crystallography of two leads. Bioorg. Med. Chem. 2017, 25, 4560-4565
  11. Sapegin, A.; Osipyan, A.; Krasavin, M. Structurally Diverse Arene-Fused Ten-Membered Lactams Accessed via Hydrolytic Imidazoline Ring Expansion. Org. Biomol. Chem. 2017, 15, 2906-2909
  12. Krasavin, M. N-(Hetero)aryl 2-imidazolines: an emerging privileged motif for contemporary drug design. Chem. Heterocycl. Comp. 2017, 53, 240-255 (Invited Contribution to Special Issue: "Privileged heterocyclic scaffolds in chemical biology and drug discovery: Synthesis and bioactivity", Guest Editor Prof. C. D. Altomare)
  13. Golubev, P.; Krasavin, M. Sterically Constrained and Encumbered: An Approach to Naturally Occurring Peptidomimetic Tetrahydropyrazino[1,2-a]indole-1,4-dione Core. Eur. J. Org. Chem. 2017, 1740-1744
  14. Galambos, J.; Bielik, A.; Krasavin, M.; Orgován, Z.; Domány, G.; Nógrádi, K.; Wágner, G.; Balogh, G.; Béni, Z.; Koti, J.; Szakács, Z.; Bobok, A.; Kolok, S.; Miko-Bakk, M.; Vastag, M.; Sághy, K.; Laszy, J.; Halász, A.; Balázs, O.; Gál, K.; Greiner, I.; Szombathelyi, Z.; Keserű, G. Discovery and Preclinical Characterization of 3-((4-(4-chlorophenyl)-7-fluoroquinoline-3-yl)sulfonyl)benzonitrile, a Novel Non-acetylenic Metabotropic Glutamate Receptor 5 (mGluR5) Negative Allosteric Modulator for Psychiatric Indications. J. Med. Chem. 2017, 60, 2470-2484
  15. Usmanova, L.; Bakulina, O.; Dar'in, D.; Krasavin, M.* Spontaneous formation of tricyclic lactones following the Castagnoli-Cushman reaction. Chemistry of Heterocyclic Compounds 2017, 53, 474-479 (Invited Contribution to Special Issue: Multicomponent Reactions in Heterocycle Synthesis, Editor Thomas J. J. Mueller)
  16. Krasavin, M.;* Korsakov, M.; Zvonaryova, Z.; Semyonychev, E.; Tuccinardi, T.; Kalinin, S.; Tanç, M.; Supuran, C. T.* Human carbonic anhydrase inhibitory profile of mono- and bis-sulfonamides synthesized via a direct sulfochlorination of 3-and 4-(hetero)arylisoxazol-5-amine scaffolds. Bioorg. Med. Chem. 2017, 25, 1914-1925
  17. Krasavin, M.;* Parchinsky, V.; Kantin, G.; Manicheva, O; Dogonadze, M.; Vinogradova, T.; Karge, B.; Brönstrup, M. New nitrofurans amenable by isocyanide multicomponent chemistry are active against multidrug-resistant and poly-resistant Mycobacterium tuberculosis. Bioorg. Med. Chem. 2017, 25, 1867-1874
  18. Bakulina, O.; Dar'in, D.; Krasavin, M.* o-Phenylenediacetic acid anhydride in the Castagnoli-Cushman reaction: extending the product space to epsilon-lactams. SYNLETT 2017, 28, 1165-1169
  19. Krasavin, M.; Lukin, A.; Bagnyukova, D.; Zhurilo, N.; Golovanov, A.; Zozulya, S.; Zahanich, I.; Daniel Moore, D.; Tikhonova, I. G. Polar aromatic periphery increases agonist potency of spirocyclic free fatty acid receptor (GPR40) agonists inspired by LY2881835. Eur. J. Med. Chem. 2017, 127, 357-368
  20. Kantin, G.; Krasavin, M. Microwave-promoted reaction of N-alk-1-enyl chloroacetamides with sodium azide unexpectedly yields 1H-imidazol-5(4H)-ones. Mendeleev Commun. 2017, 27, 95-96
  21. Kuznetsov, M. A.; Shestakov, A. N.; Zibinsky, M.; Krasavin, M.; Supuran, C. T.; Kalinin, S.; Tanc, M. Synthesis, structure and properties of N-aminosaccharin - A selective inhibitor of human carbonic anhydrase I. Tetrahedron Lett. 2017, 58, 172-174
  22. Krasavin, M.; Lukin, A.; Bagnyukova, D.; Zhurilo, N.; Zahanich, I.; Zozulya, S. Novel FFA1 (GPR40) agonists containing spirocyclic periphery: polar azine periphery as a driver of potency. J. Enzyme Inhib. Med. Chem. 2017, 32, 29-36
  23. Zubkov, F. I.; Orlova, D. N.; Zaytsev, V. P.; Voronov, A. A.; Nikitina, E. V.; Khrustalev, V. N.; Novikov, R. A.; Krasavin, M.; Varlamov. Short Approach to Pyrrolopyrazino-, Pyrrolodiazepino-Isoindoles and their Benzo Analogues via the IMDAF reaction. Curr. Org. Synth. 2017, 14, 733-746
  24. Bolotin, D. S.; Il'in, M. V.; Kolesnikov, I. E.; Suslonov, V. V.; Novozhilov, Y.; Ronzhina, O.; Krasavin, M.; Boyarskiy, V. P.; Roodt, A. Fluorescent (pyrazolyl acetoxime)ZnII complexes: synthetic, structural, and photophysical studies. Inorg. Chim. Acta 2017, 455, 9-14