Novel anti-bacterials against MRSA: Synthesis of focussed combinatorial libraries of tri-substituted 2(5H)-furanones

Eric Lattmann*, Nison Sattayasai, Carl S. Schwalbe, Suwanna Niamsanit, David C. Billington, Pornthip Lattmann, Christopher A. Langley, Harjit Singh, Simon Dunn

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Mucobromic and mucochloric acid were used as building blocks for the construction of a chemical combinatorial library of 3,4,5-trisubstituted 2(5H)-furanones. With these 2 butenolide building blocks, and eight alcohols a sublibrary of 16 dihalogenated 5-alkoxy-2(5H)-furanones was prepared. This sublibrary of 5-alkoxylated furanones was reacted with 16 amines generating a full size focussed combinatorial library of 256 individual compounds. This three dimensional combinatorial library of 3-halogen-4-amino-5-alkoxy-2(5H)-furanones was prepared around the benzimidazolyl furanone lead structure by applying a solution phase combinatorial chemistry concept. Typical representatives of the library were purified and fully characterized and one x-ray structures was recorded, additionally. The 3-bromo-4-benzimizazolyl-5-methoxy-2(5H)furanone, Br-A-l, showed an MIC of 8 μg/ml against the multiresistant Staphylococcus aureus ( MRSA). © 2006 Bentham Science Publishers Ltd.

Original languageEnglish
Pages (from-to)125-134
Number of pages10
JournalCurrent Drug Discovery Technologies
Volume3
Issue number2
DOIs
Publication statusPublished - 2006

Keywords

  • 4-amino-5-alkoxy-2(5H)- furanones
  • antibacterials
  • benzimidazolyl-lead structure
  • butenolides
  • focussed combinatorial library
  • MRSA

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