Patents

Book Chapters

Research Papers

2019

191 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, accepted 22.08.2019
190 Synofzik, J.; Dar’in, D.; Novikov, M. S.; Kantin, G.; Bakulina, O.; Krasavin, M. a-Acyl-a-diazoacetates in Transition-Metal-Free b-Lactam Synthesis. J. Org. Chem. 2019, accepted 21.08.2019
189 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
188 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, accepted 31.07.2019
187 Dar'in, D.; Kantin, G.; Krasavin, M. Practical Application of the Aqueous ‘Sulfonyl-Azide-Free’ (SAFE) Diazo Transfer Protocol to Less alpha-C-H Acidic Ketones and Esters. Synthesis 2019, accepted 31.07.2019
186 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, 111580
185 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, accepted 26/07/2019
184 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, accepted 22.07.2019
183 Safrygin, A.; Dar'in, D.; Kantin, G.; Krasavin, M. Alfa‐Diazo‐beta‐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, doi: 10.1002/ejoc.201900698
182 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, 84б 8788-8795
181 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, accepted 13.06.2019
180 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
179 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
178 Golubev, P.; Pankova, A.; Krasavin, M. “Isocyanide-less” Ugi/Intramolecular Diels-Alder reaction of 5-hydroxymethylfurfural. Tetrahedron Lett. 2019, 60б 1578-1581
177 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
176 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
175 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
174 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
173 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
172 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
171 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
170 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
169 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
168 Zhukovsky, D.; Dar'in, D.; Kantin, G.; Krasavin, M. Synthetic exploration of α-diazo γ-butyrolactams. Eur. J. Org. Chem. 2019, 2397-2400
167 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
166 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
165 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
164 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
163 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
162 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
161 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
160 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
159 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
158 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
157 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
156 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
155 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
154 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
153 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
152

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

JOURNAL COVER
151 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
150 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
149 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

148 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
147 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
146 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
145

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

JOURNAL COVER
144 Golubev, P.; Krasavin, M. N-Isocyanodialkylamines Generated In Situ for the Joullié-Ugi reaction with Indolenines. Tetrahedron Lett. 2018, 59, 3532-3536
143 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
142 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
141 Chuprun, S. S.; Kantin, G.; Krasavin, M. Synthesis and Medicinal Applications of N-Aryl-C-nitroazoles. Mini Rev. Med. Chem. 2018, 18, 1733-1752
140 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
139 Safrygin, A.; Krivosheyeva, E.; Dar'in, D.; Krasavin, M. Efficient conversion of tertiary propargylamides into imidazoles via hydroamination-cyclization. Synthesis 2018, 50, 3048-3058
138 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
137 Chupakhin, E.; Dar'in, D.; Krasavin, M. The Castagnoli-Cushman Reaction in a three-component format. Tetrahedron Letters 2018, 59, 2595-2599
136 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
135 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
134 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
133 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
132 Sapegin, A.; Krasavin, M. Efficient Suzuki-Miyaura mono-arylation of symmetrical diiodo(hetero)arenes. Tetrahedron Lett. 2018, 59, 1948-1951
131 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
130 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
129 Mikheyev, A.; Kantin, G.; Krasavin, M. Aldazines in the Castagnoli-Cushman reaction. Synthesis 2018, 50, 2076-2086
128 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
127 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
126 Guranova, N.; Dar'in, D.; Krasavin, M. Facile access to 3-unsubstituted tetrahydroisoquinolonic acids via the Castagnoli-Cushman reaction. Synthesis 2018, 50, 2076-2086
125 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
124 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
123 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

122 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
121 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
120 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
119 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
118 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
117 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
116 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
115 Kantin, G.; Chupakhin, E.; Dar'in, D.; Krasavin, M. Efficient cyclodehydration of dicarboxylic acids with oxalyl chloride. Tetrahedron Lett. 2017, 58, 3160-3163
114 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
113 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
112 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
111 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)
110 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
109 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
108 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)
107 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
106 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
105 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
104 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
103 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
102 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
101 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
100 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
99 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

2016

98 Kalinin, S.; Supuran, C. T.; Krasavin, M. Multicomponent chemistry in the synthesis of carbonic anhydrase inhibitors. J. Enzyme Inhib. Med. Chem. 2016, 31(S4), 185–199
97 Dar'in, D.; Krasavin, M.* The Chan-Evans-Lam N-Arylation of 2-Imidazolines. J. Org. Chem. 2016, 81, 12514-12519
96 Sapegin, A.; Panova, V.; Reutskaya, E.; Smirnov, A. V.; Krasavin, M. A novel, flexible strategy to construct privileged dibenzo[b,f][1,4,5]oxathiazepine-5,5-dioxides and their heterocyclic isosteres. Tetrahedron 2016, 72, 7570-7578
95 Chizhova, M.; Bakulina, O.; Dar'in, D.; Krasavin, M. New Dicarboxylic Acid Anhydride for Ambient-Temperature Castagnoli-Cushman Reaction. ChemistrySelect 2016, 1, 5487-5492
94 Krasavin, M.; Lukin, A.; Bagnyukova, D.; Zhurilo, N.; Zahanich, I.; Zozulya, I.; Ihalainen, J.; Forsberg, M. M.; Lehtonen, M.; Rautio, J.; Moore, D.; Tikhonova, I. G. Free fatty acid receptor 1 (GPR40) agonists containing spirocyclic periphery inspired by LY2881835. Bioorg. Med. Chem. 2016, 24, 5481-5494
93 Lepikhina, A.; Bakulina, O.; Dar'in, D.; Krasavin, M. The first solvent-free synthesis of privileged gamma- and delta-lactams via the Castagnoli-Cushman reaction. RSC Advances, 2016, 6, 83808 - 83813
92 Sapegin, A.; Reutskaya, E.; Smirnov, A.; Korsakov, M.; Krasavin, M. Facile entry into structurally diverse, privileged, (hetero)arene-fused N-alkoxy 3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-ones. Tetrahedron Lett. 2016, 57, 5877-5880
91 Kulyashova, A.; Krasavin, M.* Convenient modular construction of medicinally important 5-acylamino-4,5-dihydroisoxazoles featuring four elements of diversity. Tetrahedron Lett. 2016, 57, 4395-4397
90 Kantin, G.; Krasavin, M. Reactions of tetralone, 1H-tetrazol-5-amine and aromatic aldehydes under microwave irradiation: a convenient method of preparation of 5,6,7,12-tetrahydrobenzo[h]tetrazolo[5,1-b]quinazoline derivatives. Chem. Heterocycl. Compd. 2016, 52, 918-922
89 Lukin, A.; Bagnyukova, D.; Zhurilo, N.; Krasavin, M.* Gram-scale Synthesis of a Novel Core Building Block for the New GPR40 Agonist Design. Lett. Org. Chem. 2016, 13, 491-495
88 Golubev, P.; Bakulina, O.; Dar'in, D.; Krasavin, M. New Indoline-Based Constrained Peptidomimetic Motifs Obtained via the Joullié-Ugi Reaction of Indolenines. Eur. J. Org. Chem. 2016, 3969-3976
87 Lukin, A.; Bagnyukova, D.; Kalinchenkova, N.; Zhurilo, N.; Krasavin. M. Spirocyclic Amino Alcohol Building Blocks Prepared via a Prins-Type Cyclization in Aqueous Sulfuric Acid. Tetrahedron Lett. 2016, 57, 3311-3314
86 Lukin, A.; Vedekhina, T.; Tovpeko, D.; Zhurilo, N.; Krasavin, M.* Zn-Catalyzed hydrohydrazination of propargylamides with BocNHNH2: a novel entry into 1,2,4-triazine core. RSC Advances 2016, 6, 57956 - 57959
85 Dar'in, D.; Bakulina, O.; Nikolskaya, S.; Gluzdikov, I.; Krasavin, M.* The rare cis-configures trisubstitututed lactam products obtained by the Castagnoli-Cushman reaction in N,N-dimethylformamide. RSC Advances 2016, 6, 49411-49415
84 Krasavin, M.; Lukin, A.; Zhurilo, N.; Kovalenko, A.; Zahanich, I.; Zozulya, S.; Moore, D.; Tikhonova, I. G. Novel free fatty acid receptor 1 (GPR40) agonists based on 1,3,4-thiadiazole-2-carboxamide scaffold. Bioorg. Med. Chem. 2016, 24, 2954-2963
83 Supuran, C.T.; Kalinin, S.; Tanç, M.; Sarnpitak, P.; Mujumdar, P. Poulsen, S.-A.; Krasavin, M. Isoform-selective inhibitory profile of 2-imidazoline-substituted benzenesulfonamides against a panel of human carbonic anhydrases. J. Enzyme Inhib. Med. Chem. 2016, 31 (Suppl. 1), 197-202
82 Bolotin, D.S.; Novikov, A.S.; Kolesnikov, I.E.; Suslonov, V.V.; Novozhilov, Y.; Ronzhina, O.; Dorogov, M.; Krasavin, M.; Kukushkin, V. Yu. Phosphorescent Platinum(II) Complexes Featuring Chelated Acetoxime Pyrazoles: Synthetic, Structural, and Photophysical Study. ChemistrySelect 2016, 3, 456 – 461
81 Krasavin, M.;* Dar'in, D. Current diversity of cyclic anhydrides for the Castagnoli-Cushman-type formal cycloaddition reactions: prospects and challenges. Tetrahedron Lett. 2016, 57, 1635-1640. (Invited Digest Article)
80 Krasavin, M.;* Stavniichuk, R.; Zozulya, S.; Borysko, P.; Vullo, D.; Supuran, C. T.* Discovery of Strecker-type alpha-aminonitriles as a new class of human carbonic anhydrase inhibitors using differential scanning fluorimetry. J. Enzyme Inhib. Med. Chem. 2016, 31, 1707-1711
79 Kantin, G.; Krasavin, M. N-Arylation of Amidines and Guanidines: An Update (Invited Review). Curr. Org. Chem. 2016, 20, 1370-1388
78 Mishchuk, A.; Shtil, N.; Poberezhnyk, M.; Nazarenko, K.; Savchenko, T.; Tolmachev, A.; Krasavin, M. Keeping it small, polar and non-flat: diversely functionalized building blocks containing the privileged 5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]- and [1,5-a]pyridine cores. Tetrahedron Lett. 2016, 57, 1056-1059
77 Krasavin, M.; Lukin, A.; Zhurilo, N.; Kovalenko, A.; Zahanich, I.; Zozulya, S. Novel agonists of free fatty acid receptor 1 (GPR40) based on 3-(1,3,4-thiadiazol-2-yl)propanoic acid scaffold. J. Enz. Inh. Med. Chem. 2016, 31, 1404-1410
76 Lakontseva, E.; Karapetian, R.; Krasavin, M.* New Antimycobacterial Leads from Multicomponent Hydrazino-Ugi Reaction. Med. Chem. 2016, 12, 191-199
75 Lukin, A.; Karapetian, R.; Ivanenkov, Y.; Krasavin, M. Privileged 1,2,4-Oxadiazoles in Anticancer Drug Design: Novel 5-Aryloxymethyl-1,2,4-oxadiazole Leads for Prostate Cancer Therapy. Lett. Drug Des. Discov. 2016, 13, 198-204
74 Krasavin, M.;* Mujumdar, P.; Parchinsky, V.; Vinogradova, T.; Manicheva, O.; Dogonadze, M. Library of diversely substituted 2-(quinolin-4-yl)imidazolines delivers novel non-cytotoxic antitubercular leads. J. Enzyme Inhib. Med. Chem. 2016, 31, 1146-1155

2015

73 Karamysheva, K.; Reutskaya, E.; Sapegin, A.; Dorogov, M.; Krasavin, M.* Atom-economical construction of tetracyclic [1,4]oxazepines involving intramolecular arylation of a 2-imidazoline moiety. Tetrahedron Lett. 2015, 56, 5632-5636
72 Papeo, G. M. E.; Posteri, H.; Borghi, D.; Busel, A. A.; Caprera, F.; Casale, E.; Ciomei, M.; Cirla, A.; Corti, E.; D'Anello, M.; Fasolini, M.; Forte, B.; Galvani, A.; Isacchi, A.; Khvat, A.; Krasavin, M. Y.; Lupi, R.; Orsini, P.; Perego, R.; Pesenti, E.; Pezzetta, D.; Rainoldi, S.; Riccardi-Sirtori, F.; Scolaro, A.; Sola, F.; Zuccotto, F.; Felder, E. R.; Donati, D.; Montagnoli, A. Discovery of 2- [1- (4, 4- difluorocyclohexyl) piperidin- 4- yl] - 6- fluoro- 3- oxo- 2, 3- dihydro-1H-isoindole-4-carboxamide (NMS-P118): a Potent, Orally Available and Highly Selective PARP-1 Inhibitor for Cancer Therapy. J. Med. Chem. 2015, 58, 6875-6898
71 Dar'in, D.; Bakulina, O.; Chizhova, M.; Krasavin, M.* New Heterocyclic Product Space for the Castagnoli-Cushman Three-Component Reaction. Org. Lett. 2015, 17, 3930-3933
70 Iakovenko, R.; Kazakova, A.; Muzalevkiy, V.; Ivanov, A.; Boyarskaya, I. A.; Chicca, A.; Petrucci, V.; Gertsch, J.; Krasavin, M.; Starova, G. L.; Zolotarev, A. A.; Avdontceva, M. S.; Nenajdenko, V.; Vasilyev, A. Reactions of CF3-enones with arenes under superelectrophilic activation: a pathway to trans-1,3-diaryl-1-CF3-indanes, new cannabinoid receptor ligands. Org. Biomol. Chem. 2015, 13, 8827-8842
69 Krasavin, M.*; Korsakov, M.; Dorogov, M.; Tuccinardi, T.; Dedeoglu, N.; Supuran, C. T. Probing the ‘bipolar nature of the carbonic anhydrase active site: Aromatic sulfonamides containing 1,3-oxazol-5-yl moiety as picomolar inhibitors of cytosolic CA I and CA II isoforms. Eur. J. Med. Chem. 2015, 101, 334-347
68 Zahanich, I.; Kondratov, I.; Naumchyk, V.; Kheylik, Y.; Platonov, M.; Zozulya, S.; Krasavin, M.* Phenoxymethyl 1,3-Oxazoles and 1,2,4-Oxadiazoles as Potent and Selective Agonists of Free Fatty Acid Receptor 1 (GPR40). Bioorg. Med. Chem. Lett. 2015, 25, 3105-3111
67 Sarnpitak, P.; Mujumdar, P.; Taylor, P.; Cross, M.; Coster, M.J.; Gorse, A.-D.; Krasavin, M.*; Hofmann, A.* Panel docking of small-molecule libraries — Prospects to improve efficiency of lead compound discovery. Biotechnol. Adv. 2015, 33, 941-947
66 Novozhilov, Y.V.; Dorogov, M. V.; Blumina, M. V.; Smirnov, A. V.; Krasavin, M.* An improved kilogram-scale preparation of atorvastatin calcium. Chemistry Central Journal 2015, 9 (DOI: 10.1186/s13065-015-0082-7)
65 Mujumdar, P.; Sarnpitak, P.; Shetnev, A.; Dorogov, M.; Krasavin, M.* Pd-catalyzed amination of imidazolin-1-yl azines: toward a new kinase-inhibitory chemotype. Tetrahedron Lett. 2015, 56, 2827-2831
64 Sapegin, A.V.; Kalinin, S. A.; Smirnov, A. V.; Dorogov, M. V.; Krasavin, M.* Efficient Use of 1,2-Dihaloazine Synthons in Transition Metal-Free Preparation of Diverse Heterocycle-Fused 1,4-Oxazepines. Eur. J. Org. Chem. 2015, 1333-1340
63 Krasavin, M. Biologically active compounds based on the privileged 2-imidazoline scaffold: the world beyond adrenergic/imidazoline receptor modulators (Invited Review for Special Issue on Bioactive Heterocycles). Eur. J. Med. Chem. 2015, 97, 525-537
62 Krasavin, M.*; Sapegin, A.; Dorogov, M. Convenient preparation of diversely substituted fused 2-amino- and 2-mercaptonicotinonitriles under microwave irradiation. Tetrahedron Lett. 2015, 56, 56-50

2014

61 Krasavin, M.; Sosnov, A. V.; Karapetian, R.; Konstantinov, I.; Soldatkina, O.; Godovykh, E.; Zubkov, F.; Bai, R.; Hamel, E.; Gakh, A. Antiproliferative 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides, a new tubulin inhibitor chemotype. Bioorg. Med. Chem. Lett. 2014, 24, 4477-4481
60 Taheri, A.; Quinn, R. J.; Krasavin, M.* Naturally occurring scaffolds for compound library design: convenient access to bis-aryl 1-azaadamantanes carrying a vicinal amino alcohol motif. Tetrahedron Lett. 2014, 55, 5390-5393
59 Mujumdar, P.; Korsakov, M.; Dorogov, M.; Krasavin, M.* Atom-economical construction of a rare 6,7-dihydropyrido[3',2':4,5]imidazo[1,2-d][1,4]benzodiazepine scaffold. SYNLETT 2014, 25, 2323-2326
58 Sarnpitak, P.; Mujumdar, P.; Morisseau, C.; Hwang, S. H.; Hammock, B.; Iurchenko, V.; Zozulya, S.; Gavalas, A.; Geronikaki, A.; Ivanenkov, Y.; Krasavin, M.* Potent, orally available, selective COX-2 inhibitors based on 2-imidazoline core. Eur. J. Med. Chem. 2014, 84, 160-172
57 Mujumdar, P.; Sapegin, A.; Dorogov, M.; Krasavin, M.* An expeditious and atom-economic synthesis of lead-like, medicinally important 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones. Tetrahedron Lett. 2014, 55, 5732-5735
56 Sarnpitak, P.; Krasavin, M.* Convenient access to novel functionalized pyrazino[1,2-b]isoquinolin-6-one and diazepino[1,2-b]isoquinolin-7-one scaffolds via the Cushman multicomponent reaction followed by post-condensation. Tetrahedron Lett. 2014, 55, 2299-2303
55 Sapegin, A.V.; Kalinin, S. A.; Smirnov, A. V.; Dorogov, M. V.; Krasavin, M.* New tetracyclic 1,4-oxazepines constructed via practically simple tandem condensation strategy from readily available synthons. Tetrahedron 2014, 70, 1077-1083

2013

54 Golubev, V.; Zubkov, F.; Krasavin, M.* A simple, three-component synthesis of 2-aminothiazoles using trimethylsilyl isothiocyanate. Tetrahedron Lett. 2013, 54, 4844-4847
53 Mujumdar, P.; Grkovic, T.; Krasavin, M.* A simple two-step access to diversely substituted imidazo[4,5-b]pyridines and benzimidazoles from readily available 2-imidazolines. Tetrahedron Lett. 2013, 54, 3336-3340
52 Krasavin, M. Pd-Catalyzed N-arylation of 2-imidazolines provides convenient access to selective cyclooxygenase-2 inhibitors. Lett. Org. Chem. 2013, 10, 235-239
51 Sarnpitak, P.; Krasavin, M.* Synthesis of 1,2,4-triazoles employing isocyanides. Tetrahedron 2013, 69, 2289-2295
50 Gakh, A. A.; Sosnov, A. V.; Krasavin, M.; Nguyen, T. L.; Hamel, E. Identification of Diaryl 5-Amino-1,2,4-oxadiazoles as Tubulin Inhibitors: the Special Case of 3-(2-Fluorophenyl)-5-(4-methoxyphenyl)amino-1,2,4-oxadiazole. Bioorg. Med. Chem. Lett. 2013, 23, 1262-1268

2012

49 Sarnpitak, P.; Tsirulnikov, S.; Krasavin, M.* Synthesis of N1,N3-disubstituted formamidrazones via the TMSCl-promoted reaction of isocyanides with thiosemicarbazones. Tetrahedron Lett. 2012, 53, 6540-6543
48 Kulebyakin, K.; Karpova, L.; Lakontseva, E.; Krasavin, M.; Boldyrev, A. Carnosine protects neurons against oxidative stress and modulates the time profile of MAPK cascade signaling. Amino Acids 2012, 43, 91-96
47 Krasavin, M.*; Nikulnikov, M. M. Increased dipeptoid diversity resulting from post-condensational manipulation of the Ugi reaction products. Mendeleev Commun. 2012, 21, 41-42
46 Krasavin, M. Novel diversely substituted 1-heteroaryl-2-imidazolines for fragment-based drug discovery. Tetrahedron Lett. 2012, 53, 2876-2880
45 Sandulenko, Y.; Krasavin, M.* Natural Products as Templates for Bioactive Compound Libraries. 3. Novel Heterocycles and Peptidomimetics Generated from Anabasine by Isocyanide-Based Multicomponent Reactions. Chem. Heterocycl. Compd. 2012, 48, 606-612
44 Sapegin, A. V.; Kalinin, S. A.; Smirnov, A. V.; Dorogov, M. V.; Krasavin, M.* Dibenzo[b,f]pyrazolo[1,5-d][1,4]oxazepines: a facile construction of a rare heterocyclic system via tandem aromatic nucleophilic substitution - Smiles rearrangement – denitrocyclization. Synthesis 2012, 44, 2401-2407

2011

43 Konstantinov, I.; Bukhryakov, K.; Gezentsvey, Y.; Krasavin, M.* Practical Method for Parallel Synthesis of Diversely Substituted 1-Phenylpiperazines. Lett. Org. Chem. 2011, 8, 628-630
42 Parchinsky, V.; Shumsky, A.; Krasavin, M.* Microwave-assisted aza-Prins reaction. Part 1: facile preparation of natural-like 3-azabi-cyclo[3.3.1]non-6-enes. Tetrahedron Lett. 2011, 52, 7157-7160
41 Parchinsky, V.; Shumsky, A.; Krasavin, M.* Microwave-assisted aza-Prins reaction. Part 2: straightforward access to 2,6-disubstituted 1-azaadamantanes. Tetrahedron Lett. 2011, 52, 7161-7163
40 Tsaloev, A.; Ilyin, A.; Tkachenko, S.; Ivachtchenko, A.; Kravchenko, D.; Krasavin, M.* Cyclic Products of the Ugi Reaction of Aldehydo and Keto Carboxylic Acids: Chemoselective Modification. Tetrahedron Lett. 2011, 52, 1800-1803

2010

39 Ivachtchenko, A. V.; Ivanenkov Ya. A.; Kysil, V. M.; Krasavin, M.; Ilyin A. P. Multicomponent Reactions of Isocyanides in the Synthesis of Heterocycles. Russ. Chem. Rev. 2010, 79, 787-817
38 Gakh, A. A.; Anisimova N. Yu.; Kiselevsky M. V.; Sadovnikov, S. V.; Stankov, I. N.; Yudin, M. V.; Rufanov, K. A.; Krasavin, M.; Sosnov, A. V. Dihydro-resveratrol - A potent dietary polyphenol. Bioorg. Med. Chem. Lett. 2010, 20, 6149-6151
37 Krasavin, M.*; Parchinsky, V. Thiophene-containing products of the Ugi reaction in oxidation-triggered IMDA/aromatization cascade: a facile access to 3-oxoisoindolines. Tetrahedron Lett. 2010, 51, 5657-5661
36 Tsirulnikov, S.; Dmitriev, D.; Krasavin, M.* o-Aminothiophenol in Reactions with Carbonyl Compounds and Isocyanides: A Word of Caution. Synlett 2010, 1935-1938
35 Lakontseva, E.; Krasavin, M.* Diversity-oriented Pyrazol-3-one Synthesis Based on Hydrazinodipeptide-like Units Prepared via the Ugi Reaction. Tetrahedron Lett. 2010, 51, 4095-4099
34 Krasavin, M.*; Rufanov, K. A.; Sosnov, A. V.; Karapetian, R.; Godovykh, E.; Soldatkina, O.; Lavrovsky, Y.; Gakh, A. A. Discovery and SAR exploration of N-aryl-N-(3-aryl-1,2,4-oxadiazol-5-yl)amines as potential therapeutic agents for prostate cancer. Chemistry Central Journal 2010, 4
33 Nikulnikov, M.; Shumsky, A.; Krasavin, M.* Convenient Preparation of Diastereomerically Pure, Diversely Substituted Piperazine-2,5-diones from N-protected-Amino Acids. Synthesis, 2010, 2527-2532
32 Tsirulnikov, S.; Kysil, V.; Ivachtchenko, A.; Krasavin, M.* Trimethylsilyl chloride as a promoter for the Groebke-Blackburn Reaction: preparation of imidazo[2,1-b][1,3]benzothiazoles. Synth. Commun. 2010, 40, 111-119
31 Bushkova, E.; Parchinsky, V.; Krasavin, M.* Efficient entry into hydrazinopeptide-like structures via sequential Ugi reactions. Mol. Diversity 2010, 14, 493-499
30 Krasavin, M.*; Parchinsky, V.; Shumsky, A.; Konstantinov, I.; Vantskul, A. Proline-like-Turn Mimics Accessed via Ugi Reaction Involving Monoprotected Hydrazine Inputs. Tetrahedron Lett. 2010, 51, 1367-1370
29 Krasavin, M.*; Bushkova, E.; Parchinsky, V.; Shumsky, A. Hydrazinopeptide Motifs Synthesized via the Ugi Reaction: an Insight into the Secondary Structure. Synthesis 2010, 933-942

2009

28 Krasavin, M.*; Nikulnikov, M.; Tsirulnikov, S.; Kysil, V.; Ivachtchenko, A. Tert-Butyl Isocyanide as Convertible Reagent in Ugi Reaction: Microwave-Assisted Preparation of 5,6-Dihydropyrazolo[1,5-a]pyrazine-4,7-diones. Synlett 2009, 260-262
27 Krasavin, M.*; Shkavrov, S.; Parchinsky, V.; Bukhryakov, K. Imidazo[1,2-a]quinoxalines Accessed via Two Sequential Isocyanide-based Multicomponent Reactions. J. Org. Chem. 2009, 74, 2627-2629
26 Krasavin, M.*; Karapetian, R.; Konstantinov, I.; Gezentsvei, Y.; Bukhryakov, K.; Godovykh, E.; Soldatkina, O.; Lavrovsky, Y.; Sosnov, A. V.; Gakh. A. A. Discovery and Potency Optimization of 2-Amino-5-arylmethyl-1,3-thiazole Derivatives as Potential Therapeutic Agents for Prostate Cancer. Arch. Pharm. 2009, 342, 420-427
25 Aplander, K.; Ding, R.; Krasavin, M.; Lindstroem, U. M.; Wennerberg, J. Assymetric Lewis Acid Catalysis in Water: α-Amino Acids as Effective Ligands in Aqueous Biphasic Catalytic Michael Additions. Eur. J. Org. Chem. 2009, 810-821
24 Sandulenko, Y.; Komarov, A.; Krasavin, M.* Development of privileged Groebke-Blackburn-type 4-(3-aminoimidazo[1,2-a]pyridin-2-yl)benzoic acid core into a combinatorial library on solid phase. Lett. Org Chem. 2009, 6, 491-495
23 Tsirulnikov, S.; Nikulnikov. M.; Kysil, V.; Ivachtchenko, A.; Krasavin, M.* Streamlined access to 2,3-dihydropyrazino[1,2-a]indole-1,4-diones via Ugi reaction followed by microwave-assisted cyclization. Tetrahedron Lett. 2009, 50, 5529-5531
22 Krasavin, M.*; Busel, A.; Parchinsky, V. BF3•OEt2-promoted reaction of isocyanides with o-aminobenzophenones. Tetrahedron Lett. 2009, 50, 5945-5950

2008

21 Krasavin, M.*; Parchinsky, V. Z. Expedient Entry into 1,4-Dihydroquinoxalines and Quinoxalines via a Novel Variant of Isocyanide-based MCR. Synlett 2008, 645-648
20 Krasavin, M.*; Tsirulnikov, S.; Nikulnikov, M.; Kysil, V.; Ivachtchenko, A. Poorly reactive 5-piperazin-1-yl-1,3,4-thiadiazol-2-amines rendered as valid substrates for Groebke-Blackburn type multi-component reaction with aldehydes and isocyanides using TMSCl as a promoter. Tetrahedron Lett. 2008, 49, 5241-5243
19 Krasavin M.*; Konstantinov, I. O. Minimizing Side Reactions in Classical Pyrazole Synthesis from β-Oxonitriles: The Use of Acetylhydrazine. Lett. Org. Chem. 2008, 5, 594-598
18 Sandulenko, Y.; Komarov, A.; Rufanov, K.; Krasavin, M.* Greater variety in Groebke-Blackburn-type 3-arylaminoimidazo[1,2-a]azines accessed via Pd-catalyzed arylation of a primary amine precursor. Tetrahedron Lett. 2008, 49, 5990-5993
17 Krasavin, M.*; Tsirulnikov, S.; Nikulnikov, M.; Sandulenko, Y.; Bukhryakov, K. Tert-butyl isocyanide revisited as a convertible reagent in the Groebke-Blackburn reaction. Tetrahedron Lett. 2008, 49, 7318-7321

2006

16 Krasavin, M.*; Shkavrov, S.; Kravchenko, D. Preparation and Chemical Behavior of 2-(tert-Butoxycarbonyl)amino-3-bromomethyl Pyridine, a Novel Alkylating Agent. Synth. Commun. 2006, 36, 181-186
15 Parchinsky, V. Z.; Ushakova, O.; Kravchenko, D. V.; Krasavin, M.* Synthesis of 9-oxo-4,5,6,7,8,9-hexahydropyrazolo[1,5-a]pyrido[4,3-d]pyrimidine-3-carboxamides featuring regioselective formation of the tricyclic core structure. Lett. Org. Chem. 2006, 3, 715-719
14 Parchinsky, V. Z.; Koleda, V. V.; Ushakova, O.; Kravchenko, D. V.; Krasavin, M.* Air-oxidized Products of Multi-component Reactions between 3-amino-1,2,4-triazole, aromatic aldehydes and isonitriles. Tetrahedron Lett. 2006, 47, 6891-6894
13 Parchinsky, V. Z.; Koleda, V. V.; Ushakova, O.; Talismanova, T. D.; Kravchenko, D. V.; Krasavin, M.* Practical Outcome of Azaphthalimide Reduction at Various Temperatures. Lett. Org. Chem. 2006, 3, 379-383
12 Parchinsky, V. Z.; Shuvalova, O.; Ushakova, O.; Kravchenko, D. V.; Krasavin, M.* Multi-component reactions between 2-aminopyrimidine, aldehydes and isonitriles: the use of a nonpolar solvent suppresses formation of multiple products. Tetrahedron Lett. 2006, 47, 947-951
11 Shevyakov, S. V.; Davydova, Kiselyov, A.; Kravchenko, D. V.; Ivachtchenko, A. V.; Krasavin, M.* Natural products as templates for bioactive compound libraries: Part 2. Novel modifications of vasicine (peganine) core via efficient and regioselective generation of 3-lithiodeoxyvasicine and its stereoselective addition to aliphatic ketones. Nat. Prod. Res. 2006, 20, 871-881
10 Shevyakov, S. V.; Davydova, O. I.; Pershin, D. G.; Krasavin, M.*; Kravchenko, D. V.; Kiselyov, A.; Tkachenko, S. E.; Ivachtchenko, A. V. Natural products as templates for bioactive compound libraries: synthesis of biaryl derivatives of (±)-vasicine. Nat. Prod. Res. 2006, 20, 735-741
9 Ilyin, A. P.; Loseva, M. V.; Vvedensky, V. Y.; Putsykina, E. B.; Tkachenko, S. E.; Kravchenko, D. V.; Khvat, A. V.; Krasavin, M.; Ivachtchenko, A. V. One-Step Assembly of Carbamoyl-Substituted Heteroannelated [1,4]Thiazepines. J. Org. Chem. 2006, 71, 2811-2819
8 Ilyin, A.; Kysil, V.; Krasavin, M.; Kurashvili, I.; Ivachtchenko, A. V. Compexity-Enhancing Acid-Promoted Rearrangement of Tricyclic Products of Tandem Ugi 4CC/Intramolecular Diels-Alder Reaction. J. Org. Chem. 2006, 71, 9544-9547

2005

7 Ilyin, A. P.; Trifilenkov, A. S.; Kurashvili, I. D.; Krasavin, M.; Ivachtchenko, A. V. One-Step Construction of Peptidomimetic 5-Carbamoyl-4-sulfonyl-2-piperazinones. J. Comb. Chem. 2005, 7, 360-363
6 Krasavin, M.*; Kobak, V. V.; Bondarenko, T. Y.; Kravchenko, D. V. Preparation of 1-Alkyl-2-aryl-1H-imidazo[4,5-b]pyridines from 2-alkylamino-3-aminopyridines and Aromatic Aldehydes Using Air As an Oxidant. Heterocycles 2005, 65, 2189-2194
5 Krasavin, M.*; Pershin, D. G.; Larkin, D.; Kravchenko, D. Synthesis and Practical Use of 1H-1,2,3-Benzotriazole-5-carboxaldehyde for Reductive Amination. Synth. Commun. 2005, 35, 2587-2595
4 Shkavrov, S.; Popov, S.; Kravchenko, D.; Krasavin, M.* A Convenient Synthesis of 1-Amino-7-(Piperidin-4-yl)Isoquinoline. Synth. Commun. 2005, 35, 725-730

2001

3 Posner, G. H.; Jeon, H. B.; Parker, M. H.; Krasavin, M.; Paik, I.-H.; Shapiro, T. A. Antimalarial Simplified 3-Aryltrioxanes: Synthesis and Preclinical Efficacy/Toxicity Testing in Rodents. J. Med. Chem. 2001, 44, 3054-3058

2000

2 Posner, G. H.; Maxwell, J. P.; O’Dowd, H.; Krasavin, M.; Xie, S.; Shapiro, T. A. Antimalarial Sulfide, Sulfone, and Sulfonamide Trioxanes. Bioorg. Med. Chem. 2000, 8, 1361-1370

1999

1 Posner, G. H.; Ploypradith, P.; Parker, M. H.; O’Dowd, H.; Woo, S.-H.; Northrop, J.; Krasavin, M.; Dolan, P.; Kensler, T. W.; Xie, S.; Shapiro, T. A. Antimalatial, Antiproliferative, and Antitumor Activities of Artemisinin-Derived, Chemically Robust, Trioxane Dimers. J. Med. Chem. 1999, 42, 4275-4280
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