Improved Synthesis of MDL 73811 - A Potent AdoMetDC Inhibitor and Anti-Trypanosomal Compound

Anthony J. Brockway, Casey C. Cosner, Oleg A. Volkov, Margaret A. Phillips, Jef K. De Brabander

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

An improved synthesis of MDL 73811 - a potent AdoMetDC (S-adenosylmethionine decarboxylase) inhibitor and anti-trypanosomal compound with in vivo activity - has been completed in four steps from commercially available 2′,3′-O-isopropylideneadenosine. Utilization of Mitsunobu chemistry was crucial for the reliable and scalable introduction of the 5′-methylamine moiety, which was problematic using traditional activation/displacement chemistry as previously reported. All reactions in this synthesis were run on gram-scale resulting in a five-fold increase in yield over the original synthesis.

Original languageEnglish (US)
Article numberss-2016-m0105-op
Pages (from-to)2065-2068
Number of pages4
JournalSynthesis (Germany)
Volume48
Issue number13
DOIs
StatePublished - Jul 1 2016

Keywords

  • Mitsunobu reaction
  • drug discovery
  • inhibitors
  • medicinal chemistry
  • nucleosides

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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