Synthesis and biological evaluation of novel formyl-pyrazoles bearing coumarin moiety as potent antimicrobial and antioxidant agents

Bioorg Med Chem Lett. 2013 Dec 1;23(23):6406-9. doi: 10.1016/j.bmcl.2013.09.053. Epub 2013 Sep 26.

Abstract

A series of coumarin appended formyl-pyrazoles 14-18 were synthesized by a simple and accessible approach. The reaction of 8-acetyl-4-methyl-7-hydroxy coumarin 3 and phenyl hydrazine hydrochlorides 4-8 produces the intermediate compounds 8-acetyl-4-methyl-7-hydroxy coumarin hydrazones 9-13. The reaction of compounds 9-13 and DMF in the presence of POCl3 yielded formyl-pyrazoles bearing coumarin moiety 14-18 in good yield. The synthesized new compounds 14-18 and the intermediates 8-acetyl-4-methyl-7-hydroxy coumarin hydrazones 9-13 prepared were screened in vitro for their antibacterial, antifungal antioxidant activities. The compounds 12 and 17 having chloro substitution exhibited promising antifungal and antibacterial activity against the different organisms tested. The compound 17 showed remarkable DPPH radical scavenging ability.

Keywords: Antibacterial; Antifungal; Antioxidant; Heterocycles; MIC.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Coumarins / chemical synthesis*
  • Coumarins / chemistry
  • Coumarins / pharmacology*
  • Molecular Structure
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Antioxidants
  • Coumarins
  • Pyrazoles
  • coumarin