Synthesis and Biological Evaluation of Novel 2-Substituted Analogues of (-)-Pentenomycin I

Stavroula A. Zisopoulou, Spyridon Bousis, Joerg Haupenthal, Jennifer Herrmann, Rolf Mueller, Anna K. H. Hirsch, Dimitri Komiotis, John K. Gallos, Christos I. Stathakis*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

A library of novel 2-substituted derivatives of the antibiotic natural product pentenomycin I is presented. The new collection of analogues is divided in two main classes, 2-alkynyl- and 2-aryl- derivatives, which are accessed by the appropriate type of palladium-catalyzed cross-coupling reaction of the 2-iodo-protected pentenomycin I with suitable nucleophiles. The new derivatives were tested for their activity against certain types of bacteria and one of them, compound 8h , was found to exhibit significant inhibitory activity against several Gram-positive bacteria but also displayed cytotoxic activity against eukaryotic cell lines.

Original languageEnglish
Pages (from-to)475-481
Number of pages7
JournalSynlett
Volume31
Issue number5
DOIs
Publication statusPublished - 17-Mar-2020

Keywords

  • (-)-pentenomycin
  • Sonogashira
  • Suzuki
  • antimicrobial agents
  • Gram-positive bacteria
  • PENTENOMYCIN-I
  • DERIVATIVES

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