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Synthesis and antimicrobial activity of some netropsin analogues

Khalaf, A.I. and Ebrahimabadi, A.H. and Drummond, A.J. and Anthony, N.G. and Mackay, S.P. and Suckling, C.J. and Waigh, R.D. (2004) Synthesis and antimicrobial activity of some netropsin analogues. Organic and Biomolecular Chemistry, 2 (21). pp. 3119-3127. ISSN 1477-0520

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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.