TY - JOUR
T1 - Synthesis of 1,2-dihydropyridine, Arylidene, Hydrazide, and Terthienylnicotin-amidine Hydrochloride Analogs
T2 - Theoretical Studies, and Antioxidant Activity Assessment
AU - Hammouda, Mohamed M.
AU - Abed, Nadher A.
AU - Ismail, Mohamed A.
AU - Abdel-Latif, Ehab
N1 - Publisher Copyright:
© 2023 Bentham Science Publishers.
PY - 2023
Y1 - 2023
N2 - 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, Aryli-denes, and hydrazides. Our strategies were prolonged for the synthesis of novel ter-thienylnicotinamidine 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,1H-NMR,13C-NMR, MS, and elemental analysis). The theoretical studies of terthienylnicotin-amidine verified that the other atoms that carry a high density of positive values are consid-ered 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 hy-drazide analogs provided remarkable antioxidant activity (78.1, and 60.3%).
AB - 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, Aryli-denes, and hydrazides. Our strategies were prolonged for the synthesis of novel ter-thienylnicotinamidine 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,1H-NMR,13C-NMR, MS, and elemental analysis). The theoretical studies of terthienylnicotin-amidine verified that the other atoms that carry a high density of positive values are consid-ered 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 hy-drazide analogs provided remarkable antioxidant activity (78.1, and 60.3%).
KW - 1,2-Dihydropyridines
KW - Arylidenes
KW - antioxidant activity
KW - hydrazides
KW - theoretical studies
KW - α-terthienyl derivatives
UR - http://www.scopus.com/inward/record.url?scp=85169113924&partnerID=8YFLogxK
U2 - 10.2174/1385272827666230614123355
DO - 10.2174/1385272827666230614123355
M3 - Article
AN - SCOPUS:85169113924
SN - 1385-2728
VL - 27
SP - 546
EP - 556
JO - Current Organic Chemistry
JF - Current Organic Chemistry
IS - 6
ER -