Dipeptidyl α-fluorovinyl Michael acceptors: Synthesis and activity against cysteine proteases

Koen Steert, Ibrahim El-Sayed, Pieter Van der Veken, Alisa Krishtal, Christian Van Alsenoy, Gareth D. Westrop, Jeremy C. Mottram, Graham H. Coombs, Koen Augustyns, Achiel Haemers

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

The synthesis of novel dipeptidyl α-fluorovinyl sulfones using a Horner-Wadsworth-Emmons approach on N-Boc-l-phenylalaninal is described. Inhibitory assays against a Leishmania mexicana cysteine protease (CPB2.8ΔCTE) revealed low biological activity. Relative rates of Michael additions of 2′-(phenethyl)thiol with vinyl sulfone and α-fluorovinyl sulfone were determined, and ab initio calculations on several Michael acceptor model structures were performed; both were in agreement with the biological testing results.

Original languageEnglish (US)
Pages (from-to)6563-6566
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume17
Issue number23
DOIs
StatePublished - Dec 1 2007
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Keywords

  • Cysteine proteases
  • Inhibitors
  • α-Fluorovinyl Michael acceptors

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