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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).

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, in press


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


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, in press


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, in press


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, in press


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, in press


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, in press


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, in press


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.
Chemistry of Heterocyclic Compounds 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.
The Journal of Biological Chemistry, 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.
British Journal of Pharmacology, 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. 2014, 16 (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: Asymmetry 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: Asymmetry 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.
Organic and Biomolecular Chemistry, 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 (Germany), 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.
Organic and Biomolecular Chemistry, 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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