A Study On Synthesis, Biological Activities and Molecular Modelling of Some Novel Trisubstituted 1,2,4-Triazole Derivatives

Gultekin E., KOLCUOĞLU Y., AKDEMİR A., Sirin Y., BEKTAŞ H., BEKİRCAN O.

CHEMISTRYSELECT, vol.3, no.31, pp.8813-8818, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 3 Issue: 31
  • Publication Date: 2018
  • Doi Number: 10.1002/slct.201801578
  • Journal Name: CHEMISTRYSELECT
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.8813-8818
  • Keywords: Antioxidant activity, Antiurease activity, AChE activity, Molecular modelling, 1,2,4-Triazoles, ANTIOXIDANT ACTIVITIES, HELICOBACTER-PYLORI, ANTIVIRAL ACTIVITY, TRIAZOLE SCAFFOLD, INHIBITORS, UREASE, MECHANISMS, CANCER, RINGS
  • Karadeniz Technical University Affiliated: Yes

Abstract

In this study, 1-(4-substitued benzyl)-3,5-diphenyl-1H-1,2,4-triazoles (2 a-e) and ethyl(3,5-diphenyl-/H-1,2,4-triazole-1-yl) acetate (3) were synthesized starting from 3,5-diphenyl-/H1,2,4-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/phenyh-Ithiosemicarbazide (5a,b). The cyclization of the thiosemicarbazide (5a,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]-4methyl/phenyl-2,4-dihidro-3H-1,2,4-triazole-3-thiol (6a,b). Finally, the synthesized 1,2,4-triazole-3-thiols (6a,b) were converted to their 5-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 7f is very good in biochemically active compounds.