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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Research Article

Synthesis of 1,2-dihydropyridine, Arylidene, Hydrazide, and Terthienylnicotinamidine Hydrochloride Analogs: Theoretical Studies, and Antioxidant Activity Assessment

Author(s): Mohamed M. Hammouda*, Nadher A. Abed, Mohamed A. Ismail and Ehab Abdel-Latif

Volume 27, Issue 6, 2023

Published on: 13 July, 2023

Page: [546 - 556] Pages: 11

DOI: 10.2174/1385272827666230614123355

Price: $65

Abstract

In the current work, we have utilized the reactivity of N-(4-acetylphenyl)-2-(4- formylphenoxy)acetamide for the synthesis of novel series of 1,2-dihydropyridines, Arylidenes, and hydrazides. Our strategies were prolonged for the synthesis of novel terthienylnicotinamidine hydrochloride salt through a Stille coupling reaction of 6-(5'-bromo- [2,2'-bithiophen]-5-yl)nicotinonitrile with 2-tributyltin thiophene followed by treatment with lithium trimethylsilylamide and subsequent hydrolysis.

The newly prepared structures were well-elucidated by analytical and spectral data (IR, 1HNMR, 13C-NMR, MS, and elemental analysis). The theoretical studies of terthienylnicotinamidine verified that the other atoms that carry a high density of positive values are considered active centers for the electron acceptor.

The novel synthesized compounds were efficiently established by spectroscopic data and elemental analysis. The antioxidant activity of the synthesized arylidene, hydrazide, and dihydropyridine compounds was assessed by ABTS•+ free radical assay.

The results verified that the transformation of N-(4-acetylphenyl)-2-(4-formylphenoxy)acetamide (47.6%) into hydrazide analogs provided remarkable antioxidant activity (78.1, and 60.3%).

Keywords: 1, 2-Dihydropyridines, Arylidenes, hydrazides, α-terthienyl derivatives, theoretical studies, antioxidant activity.

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