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Publications for 2013-2014

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 and The Institute of Organic Chemistry.

Bogolubsky, A. V.; Moroz, Y. S.; Mykhailiuk, P. K.; Panov, D. M.; Pipko, S. E.; Konovets, A. I.; Tolmachev, A. A one-pot parallel reductive amination of aldehydes with heteroaromatic amines ACS Comb. Sci., 2014, in press

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. Structure Analysis and Conformational Transitions of the Cell Penetrating Peptide Transportan 10 in the Membrane-Bound State PLOS ONE, 2014, 9, 1-14

Trofymchuk, S.; Bezdudny, A.; Pustovit, Y.; Mykhailiuk, P. K. Synthesis of isomeric (3,3,3-trifluoropropyl)anilines Journal of Fluorine Chemistry, 2014, in press

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

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

Mykhailiuk, P. K. Generation of C2F5CHN2 In Situ and Its First Reaction: [3+2] Cycloaddition with Alkenes Chem. Eur. J., 2014, 20(17), 4942–4947

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

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

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

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

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

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

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

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

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

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

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

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

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

Slobodyanyuk, E. Y.; Artamonov, O. S.; Shishkin, O. V.; Mykhailiuk, P. K. One-Pot Synthesis of CF3-Substituted Pyrazolines/Pyrazoles from Electron-Deficient Alkenes/Alkynes and CF3CHN2 Generated in situ: Optimized Synthesis of Tris(trifluoromethyl)pyrazole European Journal of Organic Chemistry, 2014, 12, 2487–2495

2013

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

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

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

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

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

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

Dotsenko, V. V.; Frolov, K. A.; Krivokolysko, S. G.; Polovinko, V. V. Unexpected result in the reaction of 3-amino-3-thioxopropanamides with 2-anilinomethylene derivatives of 1,3-dicarbonyl compounds. synthesis of pyrimidine-5-carboxamide derivatives Chemistry of Heterocyclic Compounds, 2013, 49, 440-451

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. Stereochemical effects on the aggregation and biological properties of the fibril-forming peptide [KIGAKI]3 in membranes. Phys.Chem.Chem.Phys. 2013, 15, 8962-8971

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

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

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

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

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

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

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

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

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

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

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

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

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. Synthesis of 2- and 3-trifluoromethylmorpholines: Useful building blocks for drug discovery Tetrahedron, 2013, 69 (19), 3796-3804.

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. A convenient route to 1-alkyl-5-trifluoromethyl-1,2,3-triazole-4-carboxylic acids employing a diazo transfer reaction European Journal of Organic Chemistry, 2013, (14), 2891-2897.

Iaroshenko, V.O.; Ali, S.; Babar, T.M.; Abbasi, M.S.A.; Sosnovskikh, V.Y.; Villinger, A.; Tolmachev, A.; Langer, P. 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 Tetrahedron, 2013, 69 (15), 3167-3181.

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

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

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

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. Design, synthesis and transformation of some heteroannulated 3-aminopyridines - Purine isosteres with exocyclic nitrogen atom Tetrahedron, 2013, 69 (3), 1217-1228.



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