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RESEARCH
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2017-2018
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Publications for 2017-2018

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 and antimicrobial evaluation of 3-(4-arylthieno[2,3-d]pyrimidin-2-yl)- 2H-chromen-2-ones
Vlasov S.; Kovalenko S.; Shynkarenko P.; Krolenko K. Vlasov V.
Heterocycl. Commun. 2018, 24 (4), 237-240

The application of anthraquinone-based triazenes as equivalents of diazonium salts in reaction with methylene active compounds
Lozynskyi A.; Sabadakh O.; Luchkevich E.; Taras T.; Vynnytska, Renata, Karpenko O.; Novikov V.; Lesyk R.
Phosphorus, Sulfur Silicon Relat. Elem. 2018, 211, 193 (7), 409-414

Synthesis of Functionalized 1,4-Dioxanes with an Additional (Hetero)Aliphatic Ring
Grygorenko O.; Bondarenko A.; Tolmachev A.; Vashchenko B.
Synthesis 2018, 211, in press

Synthesis, Tautomerism, and Antiradical Activity of Novel Pteridinetrione Derivatives
Kazunin M.; Voskoboynik O.; Nosulenko I.; Berest G.; Sergeieva T.; Okovytyy S.; Karpenko O.; Priimenko B.; Kovalenko S.
J. Heterocycl. Chem. 2018, 55 (4), 1033-1041

Conformationally Constrained Mono-Fluorinated Arginine as a Cationic Label for Solid-State 19 F NMR Analysis of Membrane-Bound Peptides
Michurin O.; Tolmachova K.; Afonin S.; Babii O.; Grage S.; Ulrich A.; Komarov I.; Radchenko D.
Eur. J. Org. Chem. 2018, 27-28, 3826-3833

Diels-Alder Reaction in the Synthesis of Fluorinated (Hetero)Aromatic Compounds
Kondratov I.; Tolmachova N.; Haufe G.
Eur. J. Org. Chem. 2018, in press

Synthesis of Bi- and Polyfunctional Isoxazoles from Amino Acid Derived Halogenoximes and Active Methylene Nitriles
Chalyk B.; Hrebeniuk K.; Gavrilenko K.; Shablykin O.; Yanshyna O.; Bash D.; Mykhailiuk P.; Liashuk O.; Grygorenko O.
Eur. J. Org. Chem. 2018, 22, 2753-2761

1-(Trimethylsilyl)vinyl MIDA Boronate: A Trifunctional C2 Building Block
Ivon Y. M.; Voitenko Z. V.; Grygorenko O. O.
Synthesis 2018, in press

1-(Trimethylsilyl)vinyl MIDA Boronate: A Trifunctional C2 Building Block
Amino sulfonic acids, peptidosulfonamides and other related compounds
Grygorenko O. O.; Biitseva A. V.; Zhersh S.
Tetrahedron 2018, 4 (13), 1355-1421

Amino sulfonic acids, peptidosulfonamides and other related compounds
An Old Story in the Parallel Synthesis World: An Approach to Hydantoin Libraries
Bogolubsky A. V.; Moroz Y. S.; Savych O.; Pipko S.; Konovets A.; Platonov M. O.; Vasylchenko O. V.; Hurmach V. V.; Grygorenko O. O.
ACS Comb. Sci. 2018, 20 (1), 35-43

An Old Story in the Parallel Synthesis World: An Approach to Hydantoin Libraries
Photochemical Synthesis of 2-Azabicyclo[3.2.0]heptanes: Advanced Building Blocks for Drug Discovery. Synthesis of 2,3-Ethanoproline
Druzhenko T.; Skalenko Y.; Samoilenko M.; Denisenko A.; Zozulya S.; Borysko P. O.; Sokolenko M. I.; Tarasov A.; Mykhailiuk P. K.
J. Org. Chem. 2018, 83 (3), 1394–1401

Photochemical Synthesis of 2-Azabicyclo[3.2.0]heptanes: Advanced Building Blocks for Drug Discovery. Synthesis of 2,3-Ethanoproline
Synthesis of 8H-pyrazolo[5',1':3,4]pyrazino[2,1-b]quinazolin-8-ones
Ivon Y. M.; Voitenko Z. V.; Grygorenko O. O.
Chem. Heterocycl. Compd. 2018, 53 (11), 1242-1247

Synthesis of 8?-pyrazolo[5',1':3,4]pyrazino[2,1-b]quinazolin-8-ones
Synthesis of novel 1,2-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one derivatives
Yaremchuk I. O.; Muzychka L. V.; Smolii O. B.; Kucher O. V.; Shishkina S. V.
Tetrahedron Lett. 2018, 59 (5), 442-444

Synthesis of novel 1,2-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one derivatives

2017

Regioselective decarboxylative addition of malonic acid and its mono(thio)esters to 4-trifluoromethylpyrimidin-2(1H)-ones
Melnykov S. V.; Pataman A. S.; Dmytriv Y. V.; Shishkina S. V.; Vovk M. V.; Sukach V. A.
Beilstein J. Org. Chem. 2017, 13, 2617-2625

Regioselective decarboxylative addition of malonic acid and its mono(thio)esters to 4-trifluoromethylpyrimidin-2(1H)-ones
Cyclobutyl-Containing Rigid Analogues of Threonine: Synthesis and Physical Chemical Properties
Feskov I. O.; Chernykh A. V.; Kondratov I. S.; Klyachina M.; Daniliuc C. G.; Haufe G.
J. Org. Chem. 2017, 82 (23), 12863-12868

Cyclobutyl-Containing Rigid Analogues of Threonine: Synthesis and Physical Chemical Properties
Reduction of imidazolium salts – An approach to diazocines and diazocanes
Shvydenko T.; Nazarenko K.; Shvydenko K.; Boron S.; Gutov O.; Tolmachev A.; Kostyuk A.
Tetrahedron 2017, 73 (49), 6942-6953

Reduction of imidazolium salts – An approach to diazocines and diazocanes
Bicyclo[1.1.1]pentane-Derived Building Blocks for Click Chemistry
Kokhan S.; Valter Y. B.; Tymtsunik A.; Komarov I.; Grygorenko O. O.
Eur. J. Org. Chem. 2017, (43), 6450-6456

Bicyclo[1.1.1]pentane-Derived Building Blocks for Click Chemistry
Photochemical synthesis of 3-azabicyclo[3.2.0]heptanes: advanced building blocks for drug discovery
Denisenko A. V.; Druzhenko T.; Skalenko Y.; Samoilenko M.; Grygorenko O. O.; Zozulya S.; Mykhailiuk P. K.
J. Org. Chem. 2017, 82 (18), 9627-9636

Photochemical synthesis of 3-azabicyclo[3.2.0]heptanes: advanced building blocks for drug discovery
Synthesis of spirocyclic pyrrolidines: advanced building blocks for drug discovery
Chalyk B.; Butko M.; Yanshyna O.; Gavrilenko K.; Druzhenko T.; Mykhailiuk P.
Chem. Eur. J. 2017, 23 (66), 16782-16786

Synthesis of spirocyclic pyrrolidines: advanced building blocks for drug discovery
Selective 19F-labeling of functionalized carboxylic acids with difluoromethyl diazomethane (CF2HCHN2)
Mykhailiuk P.; Kishko I.; kubyshkin V.; Budisa N.; Cossy J.
Chem. Eur. J. 2017, 23 (54), 13279-13283

Selective 19F-labeling of functionalized carboxylic acids with difluoromethyl diazomethane (CF2HCHN2)
Synthesis of N-nitroso CHF2-pyrazolines, and transformation into CHF2-isoxazolines and pyrazoles
Lebed P.; Fenneteau J.; Wu Y.; Cossy J.; Mykhailiuk P.
Eur. J. Org. Chem. 2017, (41), 6114-6120

Synthesis of N-nitroso CHF2-pyrazolines, and transformation into CHF2-isoxazolines and pyrazoles
A peptidyl-prolyl model study: How does the electronic effect influence the amide bond conformation?
Mykhailiuk P. K.; Kubyshkin V.; Bach T.; Budisa N.
J. Org. Chem. 2017, 82 (17), 8831-8841

A peptidyl-prolyl model study: How does the electronic effect influence the amide bond conformation?
Synthesis of 6-azaspiro[4.3]alkanes: innovative scaffolds for drug discovery
Chalyk B.; Isakov A.; Butko M.; Hrebeniuk K.; Savych O.; Kucher O.; Gavrilenko K.; Druzhenko T.; Yarmolchuk V.; Zozulya S.; Mykhailiuk P.
Eur. J. Org. Chem. 2017, 31, 4530-4542

Synthesis of 6-azaspiro[4.3]alkanes: innovative scaffolds for drug discovery
A combinatorial screen of the CLOUD uncovers a synergy targeting the androgen receptor
Licciardello M. P.; Ringler A.; Markt P.; Klepsch F.; Lardeau C. H.; Sdelci S.; Schirghuber E.; Muller A. C.; Caldera M.; Wagner A.; Herzog R.; Penz T.; Schuster M.; Boidol B.; Durnberger G.; Folkvaljon Y.; Stattin P.; Ivanov V.; Colinge J.; Bock C.; Kratochwill K.; Menche J.; Bennett K. L.; Kubicek S.
Nature chemical biology 2017, 13 (7), 771-778

A combinatorial screen of the CLOUD uncovers a synergy targeting the androgen receptor
Synthesis, antioxidant and antimicrobial activities of novel thiopyrano[2,3-d]thiazoles based on aroylacrylic acids
Lozynskyi A.; Zasidko V.; Atamanyuk D.; Kaminskyy D.; Derkach H.; Karpenko O.; Ogurtsov V.; Kutsyk R.; Lesyk R.
Mol. Diver. 2017, 21 (2), 427-436

Synthesis, antioxidant and antimicrobial activities of novel thiopyrano[2,3-d]thiazoles based on aroylacrylic acids
Evaluation of Efficient and Practical Methods for the Preparation of Functionalized Aliphatic Trifluoromethyl Ethers
Sokolenko T. M.; Dronkina M. I.; Magnier E.; Yagupolskii L. M.; Yagupolskii Y. L.
Molecules 2017, 22 (5), 804

Evaluation of Efficient and Practical Methods for the Preparation of Functionalized Aliphatic Trifluoromethyl Ethers
Difluoromethyl Nitrile Oxide (CF2HCNO): A Neglected Chemical Reagent
Khutoryanskiy A.; Chalyk B.; Borysko P.; Kondratiuk A.; Mykhailiuk P.
Eur. J. Org. Chem. 2017, 27, 3935-3940

Difluoromethyl Nitrile Oxide (CF2HCNO): A Neglected Chemical Reagent
Diphytanoyl lipids as model systems for studying membrane-active peptides
Kara S.; Afonin S.; Babii O.; Tkachenko A. N.; Komarov I. V.; Ulrich A. S.
Biochimica et Biophysica Acta (BBA) - Biomembranes 2017, 1859 (10), 1828-1837

Diphytanoyl lipids as model systems for studying membrane-active peptides
Conformational Plasticity of the Cell-Penetrating Peptide SAP as Revealed by Solid-State 19F-NMR and Circular Dichroism Spectroscopies
Afonin S.; Kubyshkin V.; Mykhailiuk P. K.; Komarov I. V.; Ulrich A. S.
J. Phys. Chem. B 2017, 121 (27), 6479-6491

Conformational Plasticity of the Cell-Penetrating Peptide SAP as Revealed by Solid-State <sup>19</sup>F-NMR and Circular Dichroism Spectroscopies
1-Substituted 2-Azaspiro[3.3]heptanes: Overlooked Motifs for Drug Discovery
Kirichok A. A.; Shton I.; Kliachyna M.; Pishel I.; Mykhailiuk P. K.
Angew. Chem. Int. Ed. 2017, 56 (30), 8865-8869

1-Substituted 2-azaspiro[3.3]heptanes: overseen motifs for drug discovery
Synthesis of functionalized 4-fluoropyridazines
Feraldi-Xypolia A.; Fredj G.; Tran G.; Tsuchiya T.; Vors J.-P.; Mykhailiuk P.; Gomez Pardo D.; Cossy J.
Asian J. Org. Chem. 2017, 6 (7), 927-935

Synthesis of functionalized 4-fluoropyridazines
An Approach to 3-Oxa-7-azabicyclo[3.3.0]octanes – Bicyclic Morpholine Surrogates
Sokolenko Y. M.; Ostapchuk E. N.; Artemenko A.; Grygorenko O. O.
Synthesis 2017, 49 (14), 3112-3117

An Approach to 3-Oxa-7-azabicyclo[3.3.0]octanes – Bicyclic Morpholine Surrogates
Orientation and Location of the Cyclotide Kalata B1 in Lipid Bilayers Revealed by Solid-State NMR
Grage S. L.; Sani M.-A., Cheneval O.; Henriques S. T.; Schalck C.; Heinzmann R.; Mylne J. S.; Mykhailiuk P. K.; Afonin S.; Komarov I. V.; Separovic F.; Craik D. J.; Ulrich A. S.
Biophys. J. 2017, 112 (4), 630–642

Orientation and Location of the Cyclotide Kalata B1 in Lipid Bilayers Revealed by Solid-State NMR
CF3S(O)n-containing enaminones as precursors for the synthesis of pyrimidine-4(3H)-ones
Sokolenko L. V.; Yagupolskii Y. L.; Kumanetska L. S.; Marrot J.; Magnier E.; Lipetskij V. O.; Kalinin I. V.
Tetrahedron Lett. 2017, 58 (13), 1308–1311

CF3S(O)n-containing enaminones as precursors for the synthesis of pyrimidine-4(3H)-ones
Synthesis of Fluorinated Oxazoles by Oxidative Cyclization of Fluorinated Enamides
Shishlyk O. S.; Shcherbatiuk A. V.; Iminov R. T.; Tverdokhlebov A. V.; Tolmachev A. A.; Mykhailiuk P. K.; Biitseva A. V.
J. Fluorine Chem. 2017, 196, 88-97


Synthesis and physical chemical properties of 2-amino-4-(trifluoromethoxy)butanoic acid - a CF3O-containing analogue of natural lipophilic amino acids
Kondratov I. S.; Logvinenko I. G.; Tolmachova N. A.; Morev R. N.; Kliachyna M. A.; Clausen F.; Daniliuc C. G.; Haufe G.
Org. Biomol. Chem. 2017, 15, 672-679


Synthesis of 3-oxadiazolyl/triazolyl morpholines: Novel scaffolds for drug discovery
Tereshchenko A. D.; Myronchuk J. S.; Leitchenko L. D.; Knysh I. V.; Tokmakova G. O.; Litsis O. O.; Tolmachev A.; Liubchak K.; Mykhailiuk P.
Tetrahedron 2017, 73 (6), 750–757


Synthesis of CF2H-pyrazolines by [3+2]-cycloaddition between CF2HCHN2 and electron-deficient alkenes
Li J.; Yu X.-L.; Cossy J.; Lv S.-Y.; Zhang H.-L.; Su F.; Hai L.; Mykhailiuk P.; Wu Y.
Eur. J. Org. Chem. 2017, 2, 266-270


Polar aromatic periphery increases agonist potency of spirocyclic free fatty acid receptor (GPR40) agonists inspired by LY2881835
Krasavin M.; Lukin A.; Bagnyukova D.; Zhurilo N.; Golovanov A.; Zozulya S.; Zahanich I.; Moore D.; Tikhonova I. G.
Eur. J. Med. Chem. 2017, 127, 357-368




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