Synthesis and free radical scavenging activity of coumarin derivatives containing a 2-methylbenzothiazoline motif

Arch Pharm (Weinheim). 2011 Sep;344(9):588-94. doi: 10.1002/ardp.201000271. Epub 2011 Aug 25.

Abstract

Coumarin and benzothiazole scaffolds can be found in a number of natural or synthetic antioxidants. In an effort to develop a novel radical scavenger and potential antioxidant, a series of coumarin derivatives containing 2-methylbenzothiazoline motif and related compounds was synthesized and evaluated for their DPPH (1,1-diphenyl-2-picrylhydrazyl) and ABTS(•+) (2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radicals scavenging activities. Among them, 7-hydroxy-3-(2-methyl-2,3-dihydrobenzo[d]thiazol-2-yl)-2H-chromen-2-one (3e) has shown a significant free radical scavenging activity. From the structure-activity point of view, it was found that phenolic coumarin ring and benzothiazoline moiety in target compounds may contribute to the scavenging activity against free radicals.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Benzothiazoles / chemical synthesis*
  • Benzothiazoles / chemistry
  • Biphenyl Compounds / metabolism
  • Coumarins / chemical synthesis*
  • Coumarins / chemistry
  • Free Radical Scavengers / chemical synthesis*
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / pharmacology
  • Free Radicals
  • Picrates / metabolism
  • Structure-Activity Relationship
  • Sulfonic Acids / metabolism
  • Thiazoles / metabolism

Substances

  • Antioxidants
  • Benzothiazoles
  • Biphenyl Compounds
  • Coumarins
  • Free Radical Scavengers
  • Free Radicals
  • Picrates
  • Sulfonic Acids
  • Thiazoles
  • 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
  • 1,1-diphenyl-2-picrylhydrazyl