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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
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. Int. J. Mol. Sci.2024, 25, 769.
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. Int. J. Mol. Sci. 2024, 25, 769.
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. Int. J. Mol. Sci.2024, 25, 769.
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. Int. J. Mol. Sci. 2024, 25, 769.
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 by a three-component reaction involving aromatic aldehydes, cyanoacetamide and dithiomalon- dianilide in the presence of morpholine. The structure of 6-amino-4-(2,4-dichlorophenyl)- 7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxamide was con-firmed using X-ray crystallography. To understand the reaction mechanism in detail, density functional theory (DFT) calculations were performed with a Grimme B97-3c composite computa-tional scheme. The results revealed that the rate limiting step is a cyclization process leading to the closure of 1,4-dihydropyridine ring with an activation barrier of 28.8 kcal/mol. Some of dithiolo[3,4-b]pyridines exhibited moderate herbicide safening effects against 2,4-D . Additional-ly, ADMET parameters were calculated and molecular docking studies were performed to identify potential protein targets.
Chemistry and Materials Science, Organic Chemistry
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