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RESEARCH


Publications for 2013-2016

The publications listed below are the result of a creative joint work of Enamine chemists and our cooperation partners at ChemBioCenter, The Institute of High Technologies, The Institute of Organic Chemistry and Karlsruhe Institute of Technology (KIT).

2016

Novel free fatty acid receptor 1 (GPR40) agonists based on 1,3,4-thiadiazole-2-carboxamide scaffold
Krasavin M.; Lukin A.; Zhurilo N.; Kovalenko A.; Zahanich I.; Zozulya S.; Moore D.; Tikhonova I. G.
Biorg. Med. Chem. 2016, 24 (13), 2954-2963



1-R-2-([1,2,4]Triazolo[1,5-c]quinazoline-2-ylthio)etanon(ol)s: Synthesis, Bioluminescence Inhibition, Molecular Docking Studies, Antibacterial and Antifungal Activities
Lyudmyla M. A.; Sergiy I. K.; Oleksandr V. K.; Andrew M. K.; Volodymyr P. N.; Natalia S. F.
Curr. Comput. Aided. Drug Des. 2016, 12 (1), 29-41



Novel FFA1 (GPR40) agonists containing spirocyclic periphery: polar azine periphery as a driver of potency
Krasavin M.; Lukin A.; Bagnyukova D.; Zhurilo N.; Zahanich I.; Zozulya S.
J. Enzyme Inhib. Med. Chem. 2016, 31 (6), 1404-1410



Novel agonists of free fatty acid receptor 1 (GPR40) based on 3-(1,3,4-thiadiazol-2-yl)propanoic acid scaffold
Krasavin M.; Lukin A.; Zhurilo N.; Kovalenko A.; Zahanich I.; Zozulya S.
J. Enzyme Inhib. Med. Chem. 2016, 31 (6), 1404-1410



Discovery of Strecker-type α-aminonitriles as a new class of human carbonic anhydrase inhibitors using differential scanning fluorimetry
Krasavin M.; Stavniichuk R.; Zozulya S.; Borysko P.; Vullo D.; Supuran C. T.
J. Enzyme Inhib. Med. Chem. 2016, 31 (6), 1707-1711



Synthesis and hydrolytic cleavage of tetrazolo[1,5-c]quinazolines
Antypenko O. M.; Kovalenko S. I.; Karpenko O. V.
Synth. Commun. 2016, 46 (6), 551-555



Free fatty acid receptor 1 (GPR40) agonists containing spirocyclic periphery inspired by LY2881835
Krasavin M.; Lukin A.; Bagnyukova D.; Zhurilo N.; Zahanich I.; Zozulya S.; Ihalainen J.; Forsberg M. M.; Lehtonen M.; Rautio J.; Moore D.; Tikhonova I. G.
Biorg. Med. Chem. 2016, 24 (21), 5481-5494



Synthesis, Anticancer, and QSAR Studies of 2-Alkyl(aryl,hetaryl)quinazolin-4(3H)-thione's and [1,2,4]Triazolo[1,5-c]quinazoline-2-thione's Thioderivatives
Antypenko O. M.; Kovalenko S. I.; Karpenko O. V.; Nikitin V. O.; Antypenko L. M.
Helv. Chim. Acta 2016, 99 (8), 621-631



Reactivity of 5-endo-hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-en-3-ones and their isomerization initiated by acids and bases
Tkachenko I. V.; Tarabara I. N.; Omel’chenko I. V.; Pal’chikov V. A.
Russ. J. Org. Chem. 2016, 52 (5), 661-669



Synthesis of a new heterocyclic system: Pyrazolo[3′,4′: 5,6][1,4]diazepino[7,1-b]quinazoline
Kemskii S. V.; Hrynyshyn E. V.; Bol’but A. V.; Vovk M. V.
Russ. J. Org. Chem. 2016, 52 (4), 607-609



Sorption discrimination between secondary alcohol enantiomers by chiral alkyl-dicarboxylate MOFs
Satska Y. A.; Mikhalyova E. A.; Chernenko Z. V.; Kolotilov S. V.; Zeller M.; Komarov I. V.; Tymtsunik A. V.; Tolmachev A.; Gavrilenko K. S.; Addison A. W.
RSC Adv. 2016, 6 (96), 93707-93714



Delivering Structural Information on the Polar Face of Membrane-Active Peptides: 19F-NMR Labels with a Cationic Side Chain
Michurin O. M.; Afonin S.; Berditsch M.; Daniliuc C. G.; Ulrich A. S.; Komarov I. V.; Radchenko D. S.
Angew. Chem. Int. Ed. 2016, 55 (47), 14595–14599


Design, Synthesis, and Application of an Optimized Monofluorinated Aliphatic Label for Peptide Studies by Solid-State 19F-NMR Spectroscopy
Kokhan S. O.; Tymtsunik A. V.; Grage S. L.; Afonin S.; Babii O.; Berditsch M.; Strizhak A. V.; Bandak D.; Platonov M. O.; Komarov I. V.; Ulrich A. S.; Mykhailiuk P. K.
Angew. Chem. Int. Ed. 2016, 55 (47), 14788–14792



Synthesis of fluoroalkyl pyrazoles from in situ generated C2F5CHN2 and electron-deficient alkenes
Mykhailiuk P.; Ishchenko A.; Stepanenko V.; Cossy J.
Eur. J. Org. Chem. 2016, 33, 5485-5493

Synthesis and Physical-Chemical Properties of cis- and trans-1-Amino-3-fluoro-3-methylcyclobutanecarboxylic Acids
Chernykh A. V.; Feskov I. O.; Chernykh A. V.; Kondratov I. S.; Tolmachova N.; Radchenko D. S.; Daniliuc C. G.; Haufe G.
Eur. J. Org. Chem. 2016, 28, 4782-4786


Expanding Synthesizable Space of Disubstituted 1,2,4-Oxadiazoles
Tolmachev A.; Bogolubsky A. V.; Pipko S. E.; Grishchenko A. V.; Ushakov D. V.; Zhemera A. V.; Viniychuk O. O.; Konovets A. I.; Zaporozhets O. A.; Mykhailiuk P. K.; Moroz Y. S.
ACS Comb. Sci. 2016, 18 (10), 616-624


Does a methionine-to-norleucine substitution in PGLa influence peptide-membrane interactions?
Radchenko D. S.; Kattge S.; Kara S.; Ulrich A. S.; Afonin S.
Biochimica et Biophysica Acta (BBA) - Biomembranes 2016, 1858 (9), 2019-2027


Unexpected Reactivity of Trifluoromethyl Diazomethane (CF3CHN2): Electrophilicity of the Terminal N-Atom
Arkhipov A. V.; Arkhipov V. V.; Cossy J.; Kovtunenko V. O.; Mykhailiuk P. K.
Org. Lett. 2016, 18 (14), 3406-3409


Copper-Catalyzed O-Difluoromethylation of Functionalized Aliphatic Alcohols: Access to Complex Organic Molecules with an OCF2H group
Levchenko K.; Datsenko O. P.; Serhiichuk O.; Tolmachev A.; Iaroshenko V. O.; Mykhailiuk P. K.
J. Org. Chem. 2016, 81 (14), 5803-5813

Practical Synthesis of Fluorinated Piperidine Analogues Based on the 2-Azaspiro[3.3]heptane Scaffold
Chernykh A. V.; Tkachenko A. N.; Feskov I. O.; Daniliuc C. G.; Tolmachova N. A.; Volochnyuk D. M.; Radchenko D. S.
Synlett 2016, 27 (12), 1824-1827


Direct Photocontrol of Peptidomimetics: An Alternative to Oxygen-Dependent Photodynamic Cancer Therapy
Babii O.; Afonin S.; Garmanchuk L. V.; Nikulina V. V.; Nikolaienko T. V.; Storozhuk O. V.; Shelest D. V.; Dasyukevich O. I.; Ostapchenko L. I.; Iurchenko V.; Zozulya S.; Ulrich A. S.; Komarov I. V.
Angew. Chem. Int. Ed. 2016, 55 (18), 5493-5496


2,2,2-Trifluoroethyl Oxalates in the One-Pot Parallel Synthesis of Hindered Aliphatic Oxamides
Bogolubsky A. V.; Moroz Y. S.; Mykhailiuk P. K.; Pipko S. E.; Grishchenko A. V.; Zhemera A. V.; Konovets A. I.; Doroschuk R. A.; Dmytriv Y. V.; Zaporozhets O. A.; Tolmachev A.
Eur. J. Org. Chem. 2016, 16, 2120-2130

Convenient approach to ω-aminoalkylthiophenes
Shvydenko T.; Nazarenko K.; Shvydenko K.; Filimonchuk S.; Vlasenko Y.; Tolmachev A.; Kostyuk A
Tetrahedron Lett. 2016, 57 (17), 1909-1911


Intramolecular functional group differentiation as a strategy for the synthesis of bridged bicyclic β-amino acids
Tymtsunik A. V.; Kokhan S. O.; Ivon Y. M.; Komarov I. V.; Grygorenko O. O.
RSC Adv. 2016, 6 (27), 22737-22748


Lipase kinetic enantiomeric resolution of 1-heteroarylethanols
Kucher, O. V.; Kolodyazhnaya, A. O.; Smolii, O. B.; Nazarenko, N. K.; Kubyshkin, V.; Mykhailiuk, P. K.; Tolmachev, A. A.
Tetrahedron: Asymm 2016, 27 (7-8), 341-345


A base promoted multigram synthesis of aminoisoxazoles: valuable building blocks for drug discovery and peptidomimetics
Chalyk B. A.; Kandaurova I. Y.; Hrebeniuk K. V.; Manoilenko O. V.; Kulik I. B.; Iminov R. T.; Kubyshkin V.; Tverdokhlebov A. V.; Ablialimov O. K.; Mykhailiuk P. K.
RSC Adv. 2016, 6 (31), 25713-25723


3,4-Bis-phosphanyl-1H-pyrrole derivatives via direct electrophilic phosphanylation of 1-tert-butyl-1H-pyrrole
Smaliy, R. V.; Chaykovskaya, A. A.; Dmitriv, Y. V.; Smal, V. M.; Shtil, N. A.; Kostyuk, A. N.
Tetrahedron Lett. 2016, 57 (12), 1382-1384


Synthesis of Functionalized 2-Trifluoromethylquinolines and their Heteroaromatic Analogues
Khutoryanskiy V. V.; Biitseva A. V.; Mykhailiuk P. K.
Asian J. of Org. Chem. 2016, 5 (4), 513-520


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
Mishchuk A., Shtil N., Poberezhnyk M., Nazarenko K., Savchenko T., Tolmachev A., Krasavin M.
Tetrahedron Lett. 2016, 57 (9), 1056-1059


Direct Nucleophilic Difluoromethylation of Enolizable Ketones with CHF2TMS/HMPA
Michurin O. M.; Radchenko D. S.; Komarov I. V.
Tetrahedron 2016, 71 (10), 1351-1356


Synthesis of diverse pyrazole-4-sulfonyl chlorides starting from 2-(benzylthio)malonaldehyde
Sokolyuk, P.A.; Kondratov, I.S.; Gavrylenko, O.V.; Tolmachov, A.A.
Mol. Diver. 2016, 20 (1), 1-7


Synthesis of fluorinated building blocks based on spiro[3.3]heptane scaffold
Chernykh A. V.; Feskov I. O.; Chernykh A. V.; Daniliuc, C. G.; Tolmachova N. A.; Volochnyuk D. M.; Radchenko D. S.
Tetrahedron 2016, 72 (1), 1036-1041


2015

Novel approach for the synthesis of N-unsubstituted 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thiones
Borisov A. V.; Kovalenko S. S.; Kovalenko S. M.
Chem. Heterocycl. Compd. 2015, 51 (7), 678-681


Heterometallic Coordination Polymers Assembled from Trigonal Trinuclear Fe2Ni-Pivalate Blocks and Polypyridine Spacers: Topological Diversity, Sorption, and Catalytic Properties
Sotnik S. A.; Polunin R. A.; Kiskin M. A.; Kirillov A. M.; Dorofeeva V. N.; Gavrilenko K. S.; Eremenko I. L.; Novotortsev V. M.; Kolotilov S. V.
Inorg. Chem. 2015, 54 (11), 5169-5181


Sorption and Separation of Optical Isomers of 2-Butanol by Chiral Porous Coordination Polymers
Satska, Yu A.; Komarova, N. P.; Gavrilenko, K. S.; Manoylenko, O. V.; Chernenko, Zh V.; Kiskin, M. A.; Kolotilov, S. V.; Eremenko, I. L.; Novotortsev, V. M.
Theor. Exp. Chem. 2015, 51 (1), 45-53


Anomalous Increase of Mesopore Size in Sba-15 Type Molecular Sieve Using Solubilized Trinuclear Complex of Chromium(Iii) as Template
Shvets O. V.; Kasyan N. V.; Yaremov, P. S.; Gavrilenko K. S.; Kolotilov, S. V.
Theor. Exp. Chem. 2015, 51 (2), 133-139


Radical Reactions of Alkyl 2-Bromo-2,2-difluoroacetates with Vinyl Ethers: “Omitted” Examples and Application for the Synthesis of 3,3-Difluoro-GABA
Kondratov I. S.; Bugera M. Y.; Tolmachova N. A.; Posternak G. G.; Daniliuc C. G.; Haufe G.
J. Org. Chem. 2015, 80 (24), 12258–12264


Synthesis of racemic and enantiopure 3,4-methanonipecotic acid
Tymtsunik A. V.; Ivon Y. M.; Komarov I. V.; Grygorenko O. O.
Tetrahedron: Asymm 2015, 26 (21-22), 1268-1272


2,2,2-Trifluoroethyl Chlorooxoacetate – Universal Reagent for One-pot Parallel Synthesis of N1-aryl-N2-alkyl-substituted Oxamides
Bogolubsky, A. V.; Moroz, Y. S.; Mykhailiuk, P. K.; Pipko, S. E.; Zhemera, A. V.; Konovets, A. I.; Stepaniuk, O. O.; Myronchuk, I. S.; Dmitriv, Y. V.; Doroschuk, R. A.; Zaporozhets, O. A.; Tolmachev, A.
ACS Comb. Sci. 2015, 17 (10), 615–622


Synthesis of Cyclopropyl- and Cyclobutylpiperidines: Advanced Building Blocks for Drug Discovery
Vyzir, I. I.; Iminov, R. T.; Tverdokhlebov, A.; Tolmachev, A. A.; Shcherbatiuk, A. V.; Mykhailiuk, P. K.; Biitseva, A. V.
Synthesis 2015, 47 (24), 3963-3971


Synthesis and Physicochemical Properties of 3-Fluorocyclobutylamines
Chernykh, A. V.; Radchenko, D. S.; Chernykh, A. V.; Kondratov, I. S.; Tolmachova, N. A.; Datsenko, O. P.; Kurkunov, M. A.; Zozulya, S. X.; Kheylik, Y. P.; Bartels, K.; Daniliuc, C. G.; Haufe, G.
Eur. J. Org. Chem. 2015, 29, 6466–6471


Ring opening of cyclic thioimidates in reaction with active methylene compounds
Shvydenko, K.; Nazarenko, K.; Shvydenko, T.; Vlasenko, Y.; Tolmachev, A.; Kostyuk, A.
Tetrahedron 2015, 71 (40), 7567–7574


Phenoxymethyl 1,3-oxazoles and 1,2,4-oxadiazoles as potent and selective agonists of free fatty acid receptor 1 (GPR40)
Zahanich, I.; Kondratov, I.; Naumchyk, V.; Kheylik, Y.; Platonov, M.; Zozulya, S.; Krasavin, M.
Bioorg. Med. Chem. Lett. 2015, 25 (16), 3105–3111


One-Pot Parallel Synthesis of Alkyl Sulfides, Sulfoxides, and Sulfones
Bogolubsky, A. V.; Moroz, Y. S.; Mykhailiuk, P. K.; Ostapchuk, E. N.; Rudnichenko, A. V.; Dmytriv, Y. V.; Bondar, A. N.; Zaporozhets, O. A.; Pipko, S. E.; Doroschuk, R. A.; Babichenko, L. N.; Konovets, A. I.; Tolmachev, A.
ACS Comb. Sci. 2015, 17 (6), 348–354


Synthesis and studies on gem-fluorinated 2-azabicyclo[n.1.0]alkanes
Kubyshkin, V.; Kheylik, Y.; Mykhailiuk, P. K.
J. Fluorine Chem. 2015, 175, 73–83


Design, Synthesis, and Characterization of SO2 -Containing Azabicyclo[3.n.1]alkanes: Promising Building Blocks for Drug Discovery
Druzhenko, T.; Denisenko, O.; Kheylik, Y.; Zozulya, S.; Shishkina, S. S.; Tolmachev, A.; Mykhailiuk, P. K.
Org. Lett. 2015, 17 (8), 1922–1925


Synthesis and Structural Analysis of Angular Monoprotected Diamines Based on Spiro[3.3]heptane Scaffold
Chernykh, A. V.; Radchenko, D. S.; Grygorenko, O. O.; Daniliuc, C. G.; Volochnyuk, D. M.; Komarov, I. V.
J. Org. Chem. 2015, 80 (8), 3974–3981


In Situ Generation of Difluoromethyl Diazomethane for [3+2] Cycloadditions with Alkynes
Mykhailiuk P. K.
Angew. Chem. Int. Ed. 2015, 22, 6558–6561

Synthesis of Trifluoromethyl-Containing Polysubstituted Aromatic Compounds by Diels–Alder Reaction of Ethyl 3-Benz­amido-2-oxo-6-(trifluoromethyl)-2H-pyran-5-carboxylate
Kondratov, I. S.; Tolmachova, N. A.; Dolovanyuk, V. G.; Gerus, I. I.; Daniliuc, C-G.; Haufe, G.
Eur. J. Org. Chem. 2015, 11, 2482–2491


γ-(S)-Trifluoromethyl proline: Evaluation as a structural substitute of proline for solid state 19F-NMR peptide studies
Kubyshkin, V. S.; Afonin, S.; Kara, S.; Budisa, N.; Mykhailiuk P. K.; Ulrich, A. S.
Org. Biomol. Chem. 2015, 13, 3171-3181


Synthesis of a 2,5-Diazabicyclo[2.2.1]heptane-Derived α,β-Diamino Acid
Ivon, Y. M.; Tymtsunik, A. V.; Komarov, I. V.; Shishkin, O. V.; Grygorenko, O. O.
Synthesis 2015, 47 (08), 1123-1130


Arylation of perfluoroalkyl vinyl sulfoxides via the Heck reaction
Sokolenko, L. V.; Yagupolskii, Y. L.; Vlasenko, Y. G.; Babichenko, L. N.; Lipetskij, V. O.; Anselmi, E.; Magnier, E.
Tetrahedron Lett. 2015, 26 (10), 1259–1262


Delivery of SiC-based nanoparticles into live cells driven by cell-penetrating peptides SAP and SAP-E
Serdiuk, T.; Bakanovich, I.; Lysenko, V.; Alekseev, S. A.; Skryshevsky, V. A.; Afonin, S.; Berger, E.; Géloëna, A.; Komarov, I. V.
RSC Adv. 2015, 5, 20498-20502


Synthesis of isomeric (3,3,3-trifluoropropyl)anilines
Trofymchuk, S.; Bezdudny, A.; Pustovit, Y.; Mykhailiuk, P. K.
J. Fluorine Chem. 2015, 171, 174–176


Facile one-pot synthesis of 4-substituted semicarbazides
Bogolubsky, A. V.; Moroz, Y. S.; Mykhailiuk, P. K.; Dmytriv, Y. V.; Pipko, S. E.; Babichenko, L. N.; Konovets, A. I.; Tolmachev, A.
RSC Adv. 2015, 5, 1063-1069


The Most Reactive Amide As a Transition-State Mimic For cis–trans Interconversion
Komarov, I. V.; Yanik, S.; Ishchenko, A. Yu.; Davies, J. E.; Goodman, J. M.; Kirby A. J.
J. Am. Chem. Soc. 2015, 137 (2), 926–930


Design and Synthesis of Novel 19F-Amino Acid: A Promising 19F NMR Label for Peptide Studies
Bandak, D.; Babii, O.; Vasiuta, R.; Komarov, I. V.; Mykhailiuk, P. K.
Org. Lett. 2015, 17 (2), 226–229


Multigram Synthesis of Fluoroalkyl-Substituted Pyrazole-4-carboxylic Acids
Iminov, R. T.; Mashkov, A. V.; Vyzir, I. I.; Chalyk, B. A.; Tverdokhlebov, A. V.; Mykhailiuk, P. K.; Babichenko, L. N.; Tolmachev, A. A.; Volovenko, Y. M.; Biitseva, A.; Shishkin, O. V.; Shishkina, S. V.
Eur. J. Org. Chem. 2015, 4, 886–891


An Expedient and Practical Approach to Functionalized 3-Aza-, 3-Oxa-, and 3-Thiabicyclo[3.3.1]nonane Systems
Ishchenko, A. Y.; Yanik, S.; Rusanov, E. B.; Komarov, I. V.; Kirby, A. J.
Synthesis 2015, 47 (03), 367


2014

Synthesis of Thieno[2,3-d]imidazoles by Copper-Catalyzed Amidine Cyclization
Liubchak, K.; Tolmachev, A.; Nazarenko, K.
Synlett 2014, 25 (07), 965-968


Three-Component Synthesis of 4-Aroyl-2(1),4,5,7-Tetrahydropyrazolo[3,4-b]Pyridin-6-Ones and Their Properties
Petrova, O. N.; Zamigajlo, L. L.; Gella, I. M.; Musatov, V. I.; Shishkina, S. V.; Shishkin, O. V.; Vashchenko, E. V.; Borisov, A. V.; Lipson, V. V.
Chem. Heterocycl. Compd. 2014, 50 (4), 514-527


Role of Protein Phosphatase 1 in Dephosphorylation of Ebola Virus VP30 Protein and Its Targeting for the Inhibition of Viral Transcription
Ilinykh, P. A.; Tigabu, B.; Ivanov, A.; Ammosova, T.; Obukhov, Y.; Garron, T.; Kumari, N.; Kovalskyy, D.; Platonov, M. O.; Naumchik, V. S.; Freiberg, A. N.; Nekhai, S.; Bukreyev, A.
J. Biol. Chem. 2014, 289, 22723-22738


Potent, orally available, selective COX-2 inhibitors based on 2-imidazoline core
Sarnpitak. P.; Mujumdar, P.; Morisseau, C.; Hwang S.H.; Hammock, B; Iurchenko, V.; Zozulya, S.; Gavalas, A.; Geronikaki, A.; Ivanenkov, Y.; Krasavin, M.
Eur. J. Med. Chem. 2014, 84, 160-172


Synthesis of pyrazoline-thiazolidinone hybrids with trypanocidal activity
Havrylyuk, D.; Zimenkovsky, B.; Karpenko, O.; Grellier, P.; Lesyk, R.
Eur. J. Med. Chem. 2014, 85, 245–254


1E7-03, a low MW compound targeting host protein phosphatase-1, inhibits HIV-1 transcription
Ammosova, T.; Platonov, M,; Ivanov, A.; Saygide?er Kont, Y.; Kumari, N.; Kehn-Hall, K.; Jerebtsova, M.; Kulkarni, A. A.; Üren, A.; Kovalskyy, D.; Nekhai, S.
Br. J. Pharmacol. 2014, 171 (22), 5059-5075


How Accurately Can We Predict the Melting Points of Drug-like Compounds?
Tetko, I. V.; Sushko, Y.; Novotarskyi, S.; Patiny, L.; Kondratov, I.; Petrenko, A. E.; Charochkina, L.; Asiri, A. M.
J. Chem. Inf. Model. 2014, 54 (12), 3320–3329


Enzyme-Catalyzed Kinetic Resolution of 2,2,2-Trifluoro-1-(heteroaryl)ethanols: Experimental and Docking Studies
Kucher, O. V.; Kolodiazhnaya, A. O.; Smolii, O. B.; Prisuazhnyk, D. V.; Tolmacheva, K. A.; Zaporozhets, O. A.; Moroz, Y. S.; Mykhailiuk, P. K.; Tolmachev, A.A.
Eur. J. Org. Chem. 2014, 34, 7692–7698


Synthesis of Boc-protected 4,5-methano-β-proline
Tymtsunik, A. V.; Ivon, Y. M.; Komarov, I. V.; Grygorenko, O. O.
Tetrahedron Lett. 2014, 55 (22), 3312–3315


A one-pot parallel reductive amination of aldehydes with heteroaromatic amines
Bogolubsky, A. V.; Moroz, Y. S.; Mykhailiuk, P. K.; Panov, D. M.; Pipko, S. E.; Konovets, A. I.; Tolmachev, A.
ACS Comb. Sci. 201416 (8), 375–380


Structure Analysis and Conformational Transitions of the Cell Penetrating Peptide Transportan 10 in the Membrane-Bound State
Fanghänel, S.; Wadhwani, P.; Strandberg, E.; Verdurmen, W. P. R.; Bürck, J.; Ehni, S.; Mykhailiuk, P. K.; Afonin, S.; Gerthsen, D.; Komarov, I. V.; Brock, R.; Ulrich, A. S.
PLoS ONE 2014, 9, 1-14

Design and Synthesis of a Monofluoro-Substituted Aromatic Amino Acid as a Conformationally Restricted 19F NMR ­Label for Membrane-Bound Peptides
Tkachenko, A. N.; Mykhailiuk, P. K.; Radchenko, D. S.; Babii, O.; Afonin, S.; Ulrich, A. S.; Komarov, I. V.
Eur. J. Org. Chem. 2014, 17, 3584-3591


Synthesis of Trifluoromethyl-Substituted 3-Azabicyclo[n.1.0]alkanes: Advanced Building Blocks for Drug Discovery
Artamonov, O. S.; Slobodyanyuk, E. Y.; Volochnyuk, D. M.; Komarov, I. V.; Tolmachev, A. A.; Mykhailiuk, P. K.
Eur. J. Org. Chem. 2014, 17, 3592-3598


One-pot parallel synthesis approach to secondary amines based on the reductive amination of ketones
Bogolubsky, A. V.; Moroz, Y. S.; Pipko, S. E.; Panov, D. M.; Konovets, A. I.; Doroschuk, R.; Tolmachev, A.
Synthesis 2014, 46 (13), 1765-1772


Toward Lead-Oriented Synthesis: One-Pot Version of Castagnoli Condensation with Nonactivated Alicyclic Anhydrides
Ryabukhin, S. V.; Panov, D. M.; Granat, D. S.; Ostapchuk, E. N.; Kryvoruchko, D. V.; Grygorenko, O. O.
ACS Comb. Sci. 2014, 16 (3), 146–153


Bis(2,2,2-trifluoroethyl) carbonate as a condensing agent in one-pot, parallel synthesis of unsymmetrical aliphatic ureas
Bogolubsky, A. V.; Moroz, Y. S.; Mykhailiuk, P. K.; Granat, D. S.; Pipko, S. E.; Konovets, A. I.; Doroschuk, R.; Tolmachev, A.
ACS Comb. Sci. 2014, 16 (6), 303-308


Synthesis and Functionalization of 3-Azolylquinoxalin-2(1H)-ones
Geraschenko, O. V.; Khodakovskiya, P. V.; Shishkin, O. V.; Tolmachev, A. A.; Mykhailiuk, P. K.
Synthesis 2014, 46 (11), 1487-1492


Controlling Biological Activity with Light: Diarylethene-Containing Cyclic Peptidomimetics
Babii, O.; Afonin, S.; Berditsch, M.; Reiβer, S.; Mykhailiuk, P. K.; Kubyshkin, V. S.; Steinbrecher, T.; Ulrich, A. S.; Komarov, I. V.
Angew. Chem. Int. Ed. 2014, 53, 3392–3395


Direct Noncatalytic Electrophilic Trifluoroacetylation of Electron-Rich Pyrazoles
Yarmoliuk, D.V.; Arkhipov, V.V.; Stambirskyi, M.V.; Dmytriv, Y.V.; Shishkin, O.V.; Tolmachev, A.A.; Mykhailiuk, P.K.
Synthesis 2014, 46 (9), 1254-1260


Sulfonyl Fluorides as Alternative to Sulfonyl Chlorides in Parallel Synthesis of Aliphatic Sulfonamides
Bogolubsky, A. V.; Moroz, Y. S.; Mykhailiuk, P. K.; Pipko, S. E.; Konovets, A. I.; Sadkova, I. V.; Tolmachev, A.
ACS Comb. Sci. 2014, 16 (4), 192-197


Gram-Scale Synthesis of 3,5-Methanonipecotic Acid, a Nonchiral Bicyclic β-Amino Acid
Tymtsunik, A. V.; Bilenko, V. A.; Grygorenko, O. O.; Komarov, I. V.
Synlett 2014, 25 (3), 355-358


Conformationally restricted glutamic acid analogues: stereoisomers of 1-aminospiro[3.3]heptane-1,6-dicarboxylic acid
Chernykh, A. V.; Radchenko, D. S.; Grygorenko, O. O.; Volochnyuk, D. M.; Shishkina, S. V.; Shishkind, O. V.; Komarov, I. V.
RSC Adv. 2014, 4, 10894-10902


Synthesis of 1-(pyrrolidin-2-ylmethyl)-1H-azoles and their piperidine-derived homologues
Zhersh, S.; Karpenko, O. V.; Ripenko, V.; Tolmachev, A. A.; Grygorenko, O. O.
Cent. Eur. J. Chem. 2014, 12 (1), 67-73


Convenient synthesis of enantiopure (R-) and (S-)-3-fluoro-3-aminomethylpyrrolidines
Yarmolchuk, V. S.; Mykhalchuk, V. L.; Mykhailiuk, P. K.
Tetrahedron 2014, 70 (18), 3011-3017


Enzymatic resolution of chroman-4-ol and its core analogues with Burkholderia cepacia lipase
Kucher, O. V.; Kolodyazhnaya, A. O.; Smoliib, O. B.; Boiko, A. I.; Kubyshkin, V. S.; Mykhailiuk, P. K.; Tolmachev, A. A.
Tetrahedron: Asymm 2014, 25 (6-7), 563-567


Conformational behavior of peptides containing residues of 3-azetidinesulfonic (3AzeS) and 4-piperidinemethanesulfonic (4PiMS) acids
Grygorenko, O. O.; Zhersh, S.; Oliinyk, B. V.; Shishkin, O. V.; Tolmachev, A. A.
Tetrahedron: Asymm 2014, 25 (3), 229–237


2013

Confining the χ space of basic natural amino acids: cyclobutane-derived χ1,χ2-constrained analogues of arginine, lysine and ornithine
Radchenko, D. S.; Michurin, O. M.; Grygorenko, O. O.; Scheinpflug, K.; Dathe, M.; Komarov, I. V.
Tetrahedron 2013, 69, 505–511

1
An approach to dihydroisoindolobenzodiazepinones—three-dimensional molecular frameworks
Yaremenko, A. G.; Shelyakin, V. V.; Volochnyuk, D. M.; Rusanov, E. B.; Grygorenko, O. O.
Tetrahedron Lett.2013, 54, 1195–1197


Synthesis of New Pyrazolo[1,5-a]pyrimidines by Reaction of β,γ-Unsaturated γ-Alkoxy-α-keto Esters with N-Unsubstituted 5-Aminopyrazoles
Stepaniuk, O. O.; Matviienko, V. O.; Kondratov, I. S.; Vitruk, I. V.; Tolmachev, A. O.
Synthesis 2013, 45 (7), 925-930


Insulin receptor-related receptor as an extracellular pH sensor involved in the regulation of acid–base balance
Petrenko, A. G.; Zozulya, S. A.; Deyev, I. E.; Eladari, D.
Biochim. Biophys. Acta 2013, 1834, 2170–2175


Development of dimethyl sulfoxide solubility models using 163 000 molecules: using a domain applicability metric to select more reliable predictions
Tetko, I. V.; Novotarskyi, S.; Sushko, I.; Ivanov, V.; Petrenko, A. E.; Dieden, R.; Lebon, F.; Mathieu, B.
J. Chem. Inf. Model. 2013, 53 (8), 1990–2000


Synthesis of imidazo[1,2-a]pyrazine and imidazo[1,2-a]pyrimidine derivatives
Borisov, A. V.; Tolmachev, A. A.; Zavada, O. A.; Zhuravel’, I. A.; Kovalenko, S. N.
Chem. Heterocyc. Compd. 2013, 49, 704-711


Stereochemical effects on the aggregation and biological properties of the fibril-forming peptide [KIGAKI]3 in membranes.
Wadhwani, P.; Reichert, J.; Strandberg, E.; Burck, J.; Misiewicz, J.; Afonin, S.; Heidenreich, N.; Fanghanel, S.; Mykhailiuk, P. K.; Komarov, I. V.; Ulrich A. S.
Phys.Chem.Chem.Phys. 2013, 15, 8962-8971


Design, synthesis and application of a CF3-phenylalanine analogue as a label to study peptides by solid state 19F-NMR.
Tkachenko, A. N.; Radchenko, D. S.; Mykhailiuk, P. K.; Afonin, S.; Ulrich, A. S.; Komarov I. V.
Angew. Chem. Int. Ed. 2013, 125, 6632-6635


Incorporation of labile trans-4,5-difluoromethanoproline into a peptide as a stable label for 19F-NMR structure analysis.
Kubyshkin, V. S.; Mykhailiuk, P. K.; Afonin, S.; Grage, S. L.; Komarov, I. V.; Ulrich A. S.
J. Fluorine Chem. 2013, 152, 136-143


Synthesis and characterization of β-trifluoromethyl-substituted pyrrolidines
Yarmolchuk, V. S.; Shishkin, O. V.; Starova, V. S.; Zaporozhets, O. A.; Kravchuk, O.; Zozulya, S.; Komarov, I. V.; Mykhailiuk P. K.
Eur. J. Org. Chem. 2013, 15, 3086-3093


1-Amino-4,4-difluorocyclohexanecarboxylic acid as a promising building block for drug discovery. Design, synthesis and characterization
Mykhailiuk, P. K.; Starova, V.; Iurchenko, V.; Shishkina, S. V.; Shishkin, O. V.; Zaporozhets O.
Tetrahedron 2013, 20, 4066-4075


An easy synthesis of α-trifluoromethyl-amines from aldehydes or ketones using the Ruppert-Prakash reagent
Radchenko, D. S.; Michurin, O. M.; Chernykh, A. V.; Lukin, O.; Mykhailiuk P. K.
Tetrahedron Lett. 2013, 54, 1897-1898


Synthesis of Isomeric 6-Trifluoromethyl-3-azabicyclo[3.1.0]hexanes: Conformationally Restricted Analogues of 4-Trifluoromethylpiperidine
Artamonov, O. S.; Slobodyanyuk, E. Y.; Shishkin, O. V.; Komarov, I. V.; Mykhailiuk P. K.
Synthesis 2013, 45, 225-230


A 19F NMR Label To Substitute Polar Amino Acids in Peptides: A CF3-Substituted Analogue of Serine and Threonine.
Tkachenko, A. N.; Mykhailiuk, P. K.; Afonin, S.; Radchenko, D. S.; Kubyshkin, V. S.; Ulrich, A. S.; Komarov I. V.
Angew. Chem. Int. Ed. 2013, 52, 1486-1489


Protecting group free synthesis of carboxyl-substituted dihydropyrimidines through Biginelli reaction
Ostapchuk, E.N.; Plaskon, A.S.; Grygorenko, O.O.; Tolmachev, A.A.; Ryabukhin, S.V.
J. Heterocyclic Chem. 2013, 50 (6), 1299-1303


A facile synthesis of functionalized 1,2,6,7-tetrahydroimidazo[1,5-C] pyrimidine-3,5-diones
Lebed, P.S.; Kos, P.O.; Tolmachev, A.; Vovk, M.V.; Boyko, A.N.; Chekotylo, A.
Synthetic Commun. 2013, 43 (17), 2343-2348


A noncatalytic approach to hetaryl-annulated 1,2,4-thiadiazine-1,1-dioxides
Cherepakha, A.; Kovtunenko, V.O.; Tolmachev, A.; Lukin, O.
J. Heterocyclic Chem. 2013, 50 (5), 1071-1077


Synthesis and reactivity of 5-polyfluoroalkyl-5-deazaalloxazines
Dudkin, S.; Iaroshenko, V.O.; Sosnovskikh, V.Y.; Tolmachev, A.A.; Villinger, A.; Langer, P.
Org. Biomol. Chem. 2013, 11 (32), 5351-5361


A solution-phase parallel synthesis of alkylated guanidines from thioisocyanates and amines
Bogolubsky, A.V.; Grishchenko, A.; Pipko, S.E.; Konovets, A.; Chuprina, A.; Tolmachev, A.; Boyko, A.N.; Chekotylo, A.; Lukin, O.
Mol. Diver. 2013, 17 (3), 471-477


Synthesis of 2- and 3-trifluoromethylmorpholines: Useful building blocks for drug discovery
Shcherbatiuk, A.V.; Shyshlyk, O.S.; Yarmoliuk, D.V.; Shishkin, O.V.; Shishkina, S.V.; Starova, V.S.; Zaporozhets, O.A.; Zozulya, S.; Moriev, R., Kravchuk, O.; Manoilenko, O.; Tolmachev, A.A.; Mykhailiuk, P.K.
Tetrahedron 2013, 69 (19), 3796-3804


A convenient route to 1-alkyl-5-trifluoromethyl-1,2,3-triazole-4-carboxylic acids employing a diazo transfer reaction
Iminov, R.T.; Mashkov, A.V.; Chalyk, B.A.; Mykhailiuk, P.K.; Tverdokhlebov, A.V.; Tolmachev, A.A.; Volovenko, Y.M.; Shishkin, O.V.; Shishkina, S.V.
Eur. J. Org. Chem. 2013, (14), 2891-2897


Efficient synthesis of novel thieno[3,2-b]-, [2,3-c]- and [3,2-c]pyridones by Sonogashira coupling of bromothiophenes with terminal alkynes and subsequent intramolecular C-N bond-forming reaction
Iaroshenko, V.O.; Ali, S.; Babar, T.M.; Abbasi, M.S.A.; Sosnovskikh, V.Y.; Villinger, A.; Tolmachev, A.; Langer, P.
Tetrahedron 2013, 69 (15), 3167-3181


An efficient synthesis of 1-methyl-4,5,6,7-tetrahydro-1 H-pyrrolo[2,3-c]pyridine and its N6-substituted analogues
Nechayev, M.A., Gorobets, N.Y., Kovalenko, S.M., Tolmachev, A.A.
Synthesis 2013, 45 (7), 919-924


A facile synthesis of annulated azolo[c][1,2,4]thiadiazine S,S-dioxides
Cherepakha, A.; Kovtunenko, V.O.; Tolmachev, A.
Tetrahedron Lett. 2013, 54 (8), 986-988


Conformational behaviour of peptides containing a 2-pyrrolidinemethanesulfonic acid (2PyMS) residue
Grygorenko, O.O.; Zhersh, S.; Oliinyk, B.V.; Shishkin, O.V.; Tolmachev, A.A.
Org. Biomol. Chem. 2013, 11 (6), 975-983


Design, synthesis and transformation of some heteroannulated 3-aminopyridines - Purine isosteres with exocyclic nitrogen atom
Iaroshenko, V.O.; Vilches-Herrera, M.; Gevorgyan, A.; Mkrtchyan, S.; Arakelyan, K.; Ostrovskyi, D.; Abbasi, M.S.A.; Supe, L.; Hakobyan, A.; Villinger, A.; Volochnyuk, D.M.; Tolmachev, A.
Tetrahedron 2013, 69 (3), 1217-1228




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