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A Study On Synthesis, Biological Activities and Molecular Modelling of Some Novel Trisubstituted 1,2,4‐Triazole Derivatives
Author(s) -
Gultekin Ergun,
Kolcuoglu Yakup,
Akdemir Atilla,
Sirin Yakup,
Bektas Hakan,
Bekircan Olcay
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801578
Subject(s) - chemistry , 1,2,4 triazole , hydrazine (antidepressant) , triazole , hydrate , medicinal chemistry , antioxidant , acetylcholinesterase , organic chemistry , stereochemistry , enzyme , biochemistry
In this study, 1‐(4‐substitued benzyl)‐3,5‐diphenyl‐ 1H ‐1,2,4‐triazoles ( 2 a‐e ) and ethyl(3,5‐diphenyl‐ 1H ‐1,2,4‐triazole‐1‐yl)acetate ( 3 ) were synthesized starting from 3,5‐diphenyl‐ 1H ‐1,2,4‐triazole ( 1 ). The ethyl acetate derivative ( 3 ) was converted to 2‐(3,5‐diphenyl‐ 1H ‐1,2,4‐triazole‐1‐yl)acetohydrazide ( 4 ) in ethanolic medium with hydrazine hydrate. The reaction of the acetohydrazide ( 4 ) with suitable isothiocyanates generate 2‐[(3, 5‐diphenyl‐ 1H ‐1,2,4‐triazole‐1‐yl)acetyl]‐4‐methyl/phenyhlthiosemicarbazide ( 5 a,b ). The cyclization of the thiosemicarbazide ( 5 a,b ) in the presence of NaOH (2 M) resulted in the formation of 5‐[(3, 5‐diphenyl‐ 1H ‐1,2,4‐triazole‐1‐yl)methyl]‐4‐methyl/phenyl‐2,4‐dihidro‐3H‐1,2,4‐triazole‐3‐thiol ( 6 a,b ). Finally, the synthesized 1,2,4‐triazole‐3‐thiols ( 6 a,b ) were converted to their S‐ substituebenzyl derivatives ( 7 a‐j ). All of the synthesized compounds ( 1‐7 ) were also examined for antioxidant capacities, and antiurease and anti‐acetylcholinesterase (anti‐AChE) activities. It has been found that antioxidant capacity and anti‐urease activity of the compound 7 f is very good in biochemically active compounds.