Synthesis, antimicrobial activity and cytotoxicity of some new carbazole derivatives

J Enzyme Inhib Med Chem. 2012 Dec;27(6):868-74. doi: 10.3109/14756366.2011.622273. Epub 2011 Oct 15.

Abstract

In this work, some N-(9-Ethyl-9H-carbazole-3-yl)-2-(phenoxy)acetamide derivatives were synthesised and evaluated for their antimicrobial activity and cytotoxicity. The structural elucidation of the compounds was performed by IR, (1)H-NMR, (13)C-NMR and FAB(+)-MS spectral data and elemental analyses. The title compounds were obtained by reacting 2-chloro-N-(9-ethyl-9H-carbazole-3-yl)acetamide with some substituted phenols. The synthesised compounds were investigated for their antibacterial and antifungal activities against Micrococcus luteus, Bacillus subtilis, Pseudomonas aeruginosa, Staphylococcus aureus, Escherichia coli, Listeria monocytogenes and Candida albicans. The compounds N-(9-Ethyl-9H-carbazole-3-yl)-2-(4-ethylphenoxy)acetamide (2c) and N-(9-Ethyl-9H-carbazole-3-yl)-2-(quinolin-8-yloxy)acetamide (2n) showed notable antimicrobial activity. The compounds were also studied for their cytotoxic effects using MTT assay, and it was seen that 2n had the lowest cytotoxic activity against NIH/3T3 cells.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / pharmacology
  • Candida albicans / drug effects*
  • Candida albicans / growth & development
  • Carbazoles / chemical synthesis*
  • Carbazoles / pharmacology
  • Cell Survival / drug effects
  • Gram-Negative Bacteria / drug effects*
  • Gram-Negative Bacteria / growth & development
  • Gram-Positive Bacteria / drug effects*
  • Gram-Positive Bacteria / growth & development
  • Mice
  • Microbial Sensitivity Tests
  • Microbial Viability / drug effects
  • NIH 3T3 Cells

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Carbazoles