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
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...
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| Veröffentlicht in: | International journal of molecular sciences 2024-01, Vol.25 (2), p.769 |
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| creator | Dotsenko, Victor V Bespalov, Alexander V Sinotsko, Anna E Temerdashev, Azamat Z Vasilin, Vladimir K Varzieva, Ekaterina A Strelkov, Vladimir D Aksenov, Nicolai A Aksenova, Inna V |
| description | 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. |
| doi_str_mv | 10.3390/ijms25020769 |
| format | Article |
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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.</description><identifier>ISSN: 1422-0067</identifier><identifier>ISSN: 1661-6596</identifier><identifier>EISSN: 1422-0067</identifier><identifier>DOI: 10.3390/ijms25020769</identifier><identifier>PMID: 38255843</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Aldehydes ; Biological activity ; Blood coagulation factors ; Chemistry ; Cyclization ; Density functionals ; Experiments ; Geometry ; Molecular Docking Simulation ; NMR ; Nuclear magnetic resonance ; Oxidation ; Physiological aspects ; Protons ; Pyridine ; Pyridines ; Resveratrol ; Specific gravity</subject><ispartof>International journal of molecular sciences, 2024-01, Vol.25 (2), p.769</ispartof><rights>COPYRIGHT 2024 MDPI AG</rights><rights>2024 by the authors. Licensee MDPI, Basel, Switzerland. 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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.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>38255843</pmid><doi>10.3390/ijms25020769</doi><orcidid>https://orcid.org/0000-0001-7163-0497</orcidid><orcidid>https://orcid.org/0000-0002-8048-4740</orcidid><orcidid>https://orcid.org/0000-0002-3204-8995</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Aldehydes Biological activity Blood coagulation factors Chemistry Cyclization Density functionals Experiments Geometry Molecular Docking Simulation NMR Nuclear magnetic resonance Oxidation Physiological aspects Protons Pyridine Pyridines Resveratrol Specific gravity |
| 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 |
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