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RESEARCH
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2017
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Publications for 2017

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).

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, in press

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, in press

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, in press

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, in press

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, in press

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, in press

Synthesis of 6-azaspiro[4.3]alkanes: innovative scaffolds for drug discovery
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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