Pyridine Carboxamides Based on Sulfobetaines: Design, Reactivity, and Biological Activity
-
Published:2022-11-03
Issue:21
Volume:27
Page:7542
-
ISSN:1420-3049
-
Container-title:Molecules
-
language:en
-
Short-container-title:Molecules
Author:
Kramarova Eugene P., Borisevich Sophia S.ORCID, Khamitov Edward M.ORCID, Korlyukov Alexander A.ORCID, Dorovatovskii Pavel V., Shagina Anastasia D., Mineev Konstantin S.ORCID, Tarasenko Dmitri V., Novikov Roman A., Lagunin Alexey A.ORCID, Boldyrev IvanORCID, Ezdoglian Aiarpi A., Karpechenko Natalia Yu.ORCID, Shmigol Tatiana A.ORCID, Baukov Yuri I., Negrebetsky Vadim V.ORCID
Abstract
The synthesis of the products of the 1,3-propanesultone ring opening during its interaction with amides of pyridinecarboxylic acids has been carried out. The dependence of the yield of the reaction products on the position (ortho-, meta-, para-) of the substituent in the heteroaromatic fragment and temperature condition was revealed. In contrast to the meta- and para-substituted substrates, the reaction involving ortho-derivatives at the boiling point of methanol unexpectedly led to the formation of a salt. On the basis of spectroscopic, X-Ray, and quantum-chemical calculation data, a model of the transition-state, as well as a mechanism for this alkylation reaction of pyridine carboxamides with sultone were proposed in order to explain the higher yields obtained with the nicotinamide and its N-methyl analog compared to ortho or meta parents. Based on the analysis of ESP maps, the positions of the binding sites of reagents with a potential complexing agent in space were determined. The in silico evaluation of possible biological activity showed that the synthetized compounds revealed some promising pharmacological effects and low acute toxicity.
Funder
Russian Foundation of Basic Research Russian Science Foundation
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Reference57 articles.
1. Borozdenko, D.A., Ezdoglian, A.A., Shmigol, T.A., Gonchar, D.I., Lyakhmun, D.N., Tarasenko, D.V., Golubev, Y.V., Cherkashova, E.A., Namestnikova, D.D., Gubskiy, I.L., A Novel Phenylpyrrolidine Derivative: Synthesis and Effect on Cognitive Functions in Rats with Experimental Ishemic Stroke. Molecules, 2021. 26. 2. Study of the new 4-phenylpyrrolidinone-2 derivative pharmacokinetics and neuroprotective effect in the ischemic stroke animal model;Borozdenko;Bull. RSMU,2020 3. Borozdenko, D.A., Shmigol, T.A., Ezdoglian, A.A., Gonchar, D.I., Karpechenko, N.Y., Lyakhmun, D.N., Shagina, A.D., Cherkashova, E.A., Namestnikova, D.D., Gubskiy, I.L., The Effect of a New N-hetero Cycle Derivative on Behavior and Inflammation against the Background of Ischemic Stroke. Molecules, 2022. 27. 4. Synthesis, Molecular and Crystal Structure of Phe Notropyl;Shipov;Bull. RSMU,2006 5. Designer Two-Electron Storage Viologen Anolyte Materials for Neutral Aqueous Organic Redox Flow Batteries;DeBruler;Chem,2017
Cited by
1 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献
|
|