Synthesis and antimicrobial activity of some netropsin analogues

Org Biomol Chem. 2004 Nov 7;2(21):3119-27. doi: 10.1039/B408386P. Epub 2004 Oct 6.

Abstract

Nine novel lexitropsins were synthesized by linking two netropsin-like moieties through three different dicarboxylic acids; 9,10-dihydro-2,7-phenanthrenedicarboxylic acid; [(3-[[(carboxymethyl)amino]carbonyl]benzoyl)amino]acetic acid and indole-2,5-dicarboxylic acid. The netropsin residues were modified by the use of N-isopentylpyrrole, 5-methylthiophene or 5-isopropylthiazole heterocyclic building blocks in place of the usual N-methylpyrrole. The compounds were tested against five gram-positive bacteria: Staphylococcus aureus, Streptomyces faecalis, methicillin resistant Staphylococcus aureus, Enterobacter cloacae, Mycobacterium fortuitum, three gram-negative bacteria: Klebsiella aerogenes, Proteus vulgaris, Escherichia coli and three fungi: Aspergillus niger, Candida albicans and Aspergillus nidulans. Some of the compounds showed significant inhibitory effects on the growth of the microorganisms.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Bacteria / drug effects
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Netropsin / analogs & derivatives*
  • Netropsin / chemical synthesis
  • Netropsin / chemistry
  • Netropsin / pharmacology

Substances

  • Anti-Infective Agents
  • lexitropsin
  • Netropsin