Synthesis and antioxidant activities of acetamidomethylsulfonyl bis heterocycles-oxazolyl/thiazolyl/imidazolyl-1,3,4-oxadiazoles

Arch Pharm (Weinheim). 2013 Jul;346(7):511-20. doi: 10.1002/ardp.201300115. Epub 2013 Jun 25.

Abstract

A new class of acetamidomethylsulfonyl bis heterocycles-oxazolyl-1,3,4-oxadiazoles, -thiazolyl-1,3,4-oxadiazoles, and -imidazolyl-1,3,4-oxadiazoles were synthesized from the synthetic intermediates, methyl 2-((4-aryloxazol-2-ylcarbamoyl)methylsulfonyl)acetate, methyl 2-((4-arylthiazol-2-ylcarbamoyl)methylsulfonyl)acetate, and methyl 2-((4-aryl-1H-imidazol-2-ylcarbamoyl)methylsulfonyl)acetate. All the title compounds were tested for their antioxidant activity. The oxadiazolylmethylsulfonyloxazolylacetamide displayed excellent radical-scavenging activity when compared with the standard ascorbic acid.

Keywords: 1,3,4-Oxadiazole; Antioxidant activity; Imidazole; Oxazole; Thiazole.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemical synthesis*
  • Antioxidants / pharmacology*
  • Ascorbic Acid / chemistry
  • Benzothiazoles / chemistry
  • Biphenyl Compounds / chemistry
  • Imidazoles / chemical synthesis*
  • Imidazoles / pharmacology*
  • Molecular Structure
  • Nitric Oxide / chemistry
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / pharmacology*
  • Picrates / chemistry
  • Structure-Activity Relationship
  • Sulfonic Acids / chemistry

Substances

  • Antioxidants
  • Benzothiazoles
  • Biphenyl Compounds
  • Imidazoles
  • Oxadiazoles
  • Picrates
  • Sulfonic Acids
  • 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
  • Nitric Oxide
  • 1,1-diphenyl-2-picrylhydrazyl
  • Ascorbic Acid