7357-70-2Relevant articles and documents
Synthesis and Properties of New Fluorine-Containing Thieno[2,3-b]pyridine Derivatives
Buryi,Dotsenko,Aksenov,Aksenova
, p. 1744 - 1751 (2019)
Cyanothioacetamide reacted with 1,1,5,5-tetrafluoroacetylacetone to give 4,6-bis(difluoromethyl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile, and alkylation of the latter with α-chloroacetamides afforded 3-amino-4,6-bis(difluoromethyl)thieno[2,3-b]pyridine-2-carboxamides. The structure of the key compounds was proved using two-dimensional NMR techniques. In silico analysis of potential biological activity and bioavailability of the synthesized compounds was performed.
Synthesis and Regiospecific Bromination of (2E,4E)-5-Aryl-2-(4-arylthiazol-2-yl)penta-2,4-dienenitrile
Aksenov, N. A.,Aksenova, I. V.,Dotsenko, V. V.,Frolov, K. A.,Krivokolysko, B. S.,Krivokolysko, S. G.,Ovcharov, S. N.,Pakholka, N. A.,Shcherbakov, S. V.
, p. 606 - 613 (2021/06/02)
Abstract: The reaction of (2E,4E)-5-phenyl-2-cyano-2,4-pentadienethioamide or (E)-3-(2-nitrophenyl)acrolein and cyanothioacetamide with α-bromoketones afforded new (2E,4E)-5-aryl-2-(4-arylthiazol-2-yl)penta-2,4-dienenitriles. Direct bromination of the latter by the action of bromine in DMF proceeded regiospecifically at the C5 position of the thiazole ring without affecting the diene system and leads to the formation of new series of (2E,4E)-5-aryl-2-(5-bromo-4-arylthiazol-2-yl)penta-2,4-dienenitriles.
New Multicomponent Synthesis of Functionalized Nitriles and Esters of 6-Alkylsulfanyl-1,4-dihydronicotinic Acids
Dyachenko, V. D.,Kalashnik, I. N.
, p. 357 - 366 (2020/04/27)
Abstract: The multicomponent condensation of malononitrile, hydrogen sulfide, aryl orhetaryl aldehydes, 1,3-dicarbonyl compounds and alkylating reagents affordedfunctionalized nitriles and esters of 6-alkylsulfanyl-1,4-dihydronicotinicacids, their aromatic analogues and 1,4-dihydrothieno[2,3-b]pyridines.
Novel multicomponent synthesis of 6,7-dihydro-5H-cyclopenta[b]pyridine derivatives
Dorovatovskii, Pavel V.,Dyachenko, Ivan V.,Dyachenko, Vladimir D.,Khrustalev, Victor N.,Nenajdenko, Valentine G.
, p. 1592 - 1598 (2021/01/11)
[Figure not available: see fulltext.] The multicomponent condensation of malononitrile, hydrogen sulfide, aldehydes, 1-(cyclopent-1-en-1-yl)pyrrolidine, and alkylating agents leads to the formation of 6,7-dihydro-5H-cyclopenta[b]pyridine derivatives. The structure of a number of heterocycles obtained on their basis was studied by X-ray structural analysis.
Synthesis and Properties of 4,6-Dimethyl-5-pentyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile and 3-Amino-4,6-dimethyl-5-pentylthieno[2,3-b]pyridines
Buryi,Dotsenko,Aksenov,Aksenova,Krivokolysko,Dyadyuchenko
, p. 1575 - 1585 (2019/10/14)
The reaction of 3-pentylpentane-2,4-dione with cyanothioacetamide afforded 4,6-dimethyl-5-pentyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile. Alkylation of the latter led to the formation of 2-alkylsulfanyl-4,6-dimethyl-5-pentylpyridine-3-carbonitriles or 3-amino-4,6-dimethyl-5-pentylthieno[2,3-b]pyridines, depending on the alkylating agent and reaction conditions. The structures of the key compounds were proved by 2D NMR spectroscopy and X-ray analysis. Biological activity of the synthesized compounds was evaluated in silico. Some compounds were experimentally found to stimulate growth of sunflower seedlings.
Structure-activity relationships of privileged structures lead to the discovery of novel biased ligands at the dopamine D2 receptor
Szabo, Monika,Klein Herenbrink, Carmen,Christopoulos, Arthur,Lane, J. Robert,Capuano, Ben
, p. 4924 - 4939 (2014/07/07)
Biased agonism at GPCRs highlights the potential for the discovery and design of pathway-selective ligands and may confer therapeutic advantages to ligands targeting the dopamine D2 receptor (D2R). We investigated the determinants of efficacy, affinity, and bias for three privileged structures for the D2R, exploring changes to linker length and incorporation of a heterocyclic unit. Profiling the compounds in two signaling assays (cAMP and pERK1/2) allowed us to identify and quantify determinants of biased agonism at the D2R. Substitution on the phenylpiperazine privileged structures (2-methoxy vs 2,3-dichloro) influenced bias when the thienopyridine heterocycle was absent. Upon inclusion of the thienopyridine unit, the substitution pattern (4,6-dimethyl vs 5-chloro-6-methoxy-4-methyl) had a significant effect on bias that overruled the effect of the phenylpiperazine substitution pattern. This latter observation could be reconciled with an extended binding mode for these compounds, whereby the interaction of the heterocycle with a secondary binding pocket may engender bias.
HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
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Paragraph 0174 - 0175, (2014/05/24)
Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.
Inhibitors of tick-borne flavivirus reproduction from structure-based virtual screening
Osolodkin, Dmitry I.,Kozlovskaya, Liubov I.,Dueva, Evgenia V.,Dotsenko, Victor V.,Rogova, Yulia V.,Frolov, Konstantin A.,Krivokolysko, Sergey G.,Romanova, Ekaterina G.,Morozov, Alexey S.,Karganova, Galina G.,Palyulin, Vladimir A.,Pentkovski, Vladimir M.,Zefirov, Nikolay S.
, p. 869 - 874 (2013/10/01)
Flaviviruses form a large family of enveloped viruses affecting millions of people over the world. To date, no specific therapy was suggested for the infected people, making the treatment exclusively symptomatic. Several attempts were performed earlier for the design of fusion inhibitors for mosquito-borne flaviviruses, whereas for the tick-borne flaviviruses such design had not been performed. We have constructed homology models of envelope glycoproteins of tick-transmitted flaviviruses with the detergent binding pocket in the open state. Molecular docking of substituted 1,4-dihydropyridines and pyrido[2,1-b][1,3,5]thiadiazines was made against these models, and 89 hits were selected for the in vitro experimental evaluation. Seventeen compounds showed significant inhibition against tick-borne encephalitis virus, Powassan virus, or Omsk hemorrhagic fever virus in the 50% plaque reduction test in PEK cells. These compounds identified through rational design are the first ones possessing reproduction inhibition activity against tick-borne flaviviruses.
On the regioselectivity of the reaction of cyanothioacetamide with 2-acetylcyclo-hexanone, 2-acetylcyclopentanone, and 2-acetyl-1-(morpholin-4-yl)- 1-cycloalkenes
Dotsenko,Krivokolysko,Polovinko,Litvinov
experimental part, p. 309 - 319 (2012/09/11)
It has been established that the interaction of cyanothioacetamide with 2-acetylcyclohexanone, 2-acetylcyclopentanone, or their enamines (2-acetyl-1-(morpholin-4-yl)-1-cycloalkenes) contrary to the literature data have a non-regiospecific character and leads to the formation of mixtures of 3-cyano-4-methyl-5,6-tri(tetra)methylenepyridine-2(1H)-thiones and 3-cyano-6-methyl-4,5-tri(tetra)methylene-pyridine-2(1H)-thiones with a predominance of the latter.
N-hetaryl-2-cyanoacetamides in the synthesis of substituted (E)-N-hetaryl-2-cyanoacrylamides, (E)-N-alkyl-N-hetaryl-2-cyanoacrylamides, and 6-amino-2-oxo-4-phenyl-1-(pyridin-2-yl)-1,2-dihydropyridine-3,5-dicarbonitriles
Dyachenko,Dyachenko,Rusanov
, p. 83 - 89 (2007/10/03)
Knoevenagel condensation of N-hetaryl-substituted cyanoacetamides with aldehydes gave the corresponding (E)-N-hetaryl-2-cyanoacrylamides which were converted into (E)-N-alkyl-N-hetaryl-2-cyanoacrylamides and 6-amino-2-oxo-4- phenyl-1-(pyridin-2-yl)-1,2-dihydropyridine-3,5-dicarbonitriles. The structure of (E)-N-(pyridin-2-yl)-2-cyano-3-phenylprop-2-enamide was determined by X-ray analysis.
