Synthesis and biological evaluation of novel N-substituted 1H-dibenzo[a,c]carbazole derivatives of dehydroabietic acid as potential antimicrobial agents

Bioorg Med Chem Lett. 2014 Jan 1;24(1):328-31. doi: 10.1016/j.bmcl.2013.11.009. Epub 2013 Nov 16.

Abstract

A series of new N-substituted 1H-dibenzo[a,c]carbazole derivatives were synthesized from dehydroabietic acid, and their structures were characterized by IR, (1)H NMR and HRMS spectral data. All compounds were evaluated for their antibacterial and antifungal activities against four bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas fluorescens) and three fungi (Candida albicans, Candida tropicalis and Aspergillus niger) by serial dilution technique. Some of the synthesized compounds displayed pronounced antimicrobial activity against tested strains with low MIC values ranging from 0.9 to 15.6μg/ml. Among them, compounds 6j and 6r exhibited potent inhibitory activity comparable to reference drugs amikacin and ketoconazole.

Keywords: 1H-Dibenzo[a,c]carbazole; Antibacterial activity; Antifungal activity; Dehydroabietic acid; Synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abietanes / chemical synthesis
  • Abietanes / chemistry
  • Abietanes / pharmacology*
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Bacteria / drug effects*
  • Carbazoles / chemistry*
  • Dose-Response Relationship, Drug
  • Fungi / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • 1H-dibenzo(a,c)carbazole
  • Abietanes
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Carbazoles
  • dehydroabietic acid