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2013-2014
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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, The Institute of Organic Chemistry and Karlsruhe Institute of Technology (KIT).

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

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


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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