Synthesis and evaluation of stereopure α-trifluoromethyl-malic hydroxamates as inhibitors of matrix metalloproteinases

Monica Sani, Dorina Belotti, Raffaella Giavazzi, Walter Panzeri, Alessandro Volonterio, Matteo Zanda

Research output: Contribution to journalArticlepeer-review

Abstract

The total synthesis of trifluoromethyl (Tfm) analogs of known nanomolar matrix metalloproteinases (MMPs) inhibitors has been performed. The synthetic protocol is based on a moderately stereoselective aldol reaction of trifluoropyruvate with an N-acyl-oxazolidin-2-thione for the construction of the core α-Tfm-malic unit. Both the diastereomeric forms of the target α-Tfm-malic hydroxamates showed micromolar inhibitory potency toward MMP-2 and 9, with a substantial drop with respect to the parent unfluorinated compounds.

Original languageEnglish
Pages (from-to)1611-1615
Number of pages5
JournalTetrahedron Letters
Volume45
Issue number8
DOIs
Publication statusPublished - Feb 16 2004

Keywords

  • Fluorine
  • Matrix metalloproteinases
  • Peptidomimetics

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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