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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).

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, in press


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
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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