Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

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

Victor V. Dotsenko
* ,
Alexander V. Bespalov
* ,
Anna E. Sinotsko
,
Azamat Z. Temerdashev
ORCID logo ,
Vladimir K. Vasilin
,
Ekaterina A. Varzieva
ORCID logo ,
Vladimir D. Strelkov
,
Nicolai A. Aksenov
,
Inna V. Aksenova
Version 1 : Received: 6 December 2023 / Approved: 7 December 2023 / Online: 7 December 2023 (07:07:11 CET)

A peer-reviewed article of this Preprint also exists.

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.

Keywords

heterocyclization; Michael addition; dithiomalondiamides; dithiolo[3,4-b]pyridines; DFT calculations; reaction mechanism studies; herbicide safeners; molecular docking; ADMET properties.

Subject

Chemistry and Materials Science, Organic Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Download PDF Download Supplementary

Comments (0)

We encourage comments and feedback from a broad range of readers. See criteria for comments and our Diversity statement.

Leave a public comment
Send a private comment to the author(s)
* All users must log in before leaving a comment
Views 0
Downloads 0
Comments 0
Metrics 0
Get PDF Supplementary Files Cite Share 0
Bookmark BibSonomy Mendeley Reddit Delicious
×
Alerts
Notify me about updates to this article or when a peer-reviewed version is published.
We use cookies on our website to ensure you get the best experience.
Read more about our cookies here.