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Title: 6-Amino-4-aryl-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxamides: Synthesis, Biological Activity, Quantum Chemical Studies and In Silico Docking Studies
Authors: Dotsenko, V. V.
Доценко, В. В.
Aksenov, N. A.
Аксенов, Н. А.
Aksenova, I. V.
Аксенова, И. В.
Keywords: ADMET properties;Reaction mechanism studies;Molecular docking;DFT calculations;Dithiolo[3,4-b]pyridines;Dithiomalondiamides;Herbicide safeners;Heterocyclization;Michael addition
Issue Date: 2024
Citation: Dotsenko, V.V., Bespalov, A.V., Sinotsko, A.E., Temerdashev, A.Z., Vasilin, V.K., Varzieva, E.A., Strelkov, V.D., Aksenov, N.A., Aksenova, I.V. 6-Amino-4-aryl-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxamides: Synthesis, Biological Activity, Quantum Chemical Studies and In Silico Docking Studies // International Journal of Molecular Sciences. - 2024. - 25 (2). - статья № 769. - DOI: 10.3390/ijms25020769
Series/Report no.: International Journal of Molecular Sciences
Abstract: New [1,2]dithiolo[3,4-b]pyridine-5-carboxamides were synthesized through the reaction of dithiomalondianilide (N,N′-diphenyldithiomalondiamide) with 3-aryl-2-cyanoacrylamides or via a three-component reaction involving aromatic aldehydes, cyanoacetamide and dithiomalondianilide in the presence of morpholine. The structure of 6-amino-4-(2,4-dichloro- phenyl)-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxamide was confirmed using X-ray crystallography. To understand the reaction mechanism in detail, density functional theory (DFT) calculations were performed with a Grimme B97-3c composite computational scheme. The results revealed that the rate-limiting step is a cyclization process leading to the closure of the 1,4-dihydropyridine ring, with an activation barrier of 28.8 kcal/mol. Some of the dithiolo[3,4-b]pyridines exhibited moderate herbicide safening effects against 2,4-D. Additionally, ADMET (Absorption, Distribution, Metabolism, Excretion, Toxicity) parameters were calculated and molecular docking studies were performed to identify potential protein targets.
Appears in Collections:Статьи, проиндексированные в SCOPUS, WOS

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