Synthesis and antimicrobial activity of some netropsin analogues

A.I. Khalaf, A.H. Ebrahimabadi, A.J. Drummond, N.G. Anthony, S.P. Mackay, C.J. Suckling, R.D. Waigh

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16 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)3119-3127
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume2
Issue number21
DOIs
Publication statusPublished - 10 Sep 2004

Keywords

  • antimicrobial activity
  • netropsin analogues
  • dicarboxylic acids
  • staphylococcus aureus
  • streptomyces faecalis
  • methicillin resistant staphylococcus aureus
  • enterobacter cloacae
  • mycobacterium fortuitum
  • pure and applied chemistry

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    Khalaf, A. I., Ebrahimabadi, A. H., Drummond, A. J., Anthony, N. G., Mackay, S. P., Suckling, C. J., & Waigh, R. D. (2004). Synthesis and antimicrobial activity of some netropsin analogues. Organic and Biomolecular Chemistry, 2(21), 3119-3127. https://doi.org/10.1039/b408386p