Synthesis and Study of alpha-Glucosidase Inhibitory, Antimicrobial and Antioxidant Activities of Some Benzimidazole Derivatives Containing Triazole, Thiadiazole, Oxadiazole, and Morpholine Rings

Mentese E., Ulker S., Kahveci B.

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, vol.50, no.12, pp.1671-1682, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 50 Issue: 12
  • Publication Date: 2015
  • Doi Number: 10.1007/s10593-015-1637-1
  • Journal Name: CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1671-1682
  • Karadeniz Technical University Affiliated: Yes

Abstract

A new series of 2-(4-bromobenzyl)- and 2-(4-fluorobenzyl)-1H-benzimidazole derivatives containing 1,2,4-triazole, 1,3,4-thiadiazole, 1,3,4-oxadiazole, and morpholine rings has been synthesized. The structures of the newly synthesized compounds were confirmed by H-1 and C-13 NMR and mass spectra, and all substances have been screened for their alpha-glucosidase inhibitory, antimicrobial and antioxidant activities. Hydrazide, oxadiazole, thiosemicarbazide, and 1,2,4-triazole-3-thiol derivatives showed very good ABTS scavenging activities (IC50 1.94-4.79 mu M). Oxadiazole and thiosemicarbazide derivatives also revealed notable DPPH scavenging activity. 5-[(2-(4-Bromobenzyl)-1H-benzimidazol-1-yl)methyl]-1,3,4-oxadiazole-2-thiol was found to be more potent than acarbose. 2-(4-Fluorobenzyl)-1H-benz- imidazole was effective against both Gram-positive and Gram-negative bacteria, especially, M. smegmatis.