Chemoenzymatic synthesis of functionalized cyclohexylglycines and alpha-methylcyclohexylglycines via Kazmaier-Claisen rearrangement

Bioorg Med Chem Lett. 2001 Mar 12;11(5):627-9. doi: 10.1016/s0960-894x(01)00013-0.

Abstract

The synthesis of homochiral functionalized cyclohexylglycines and alpha-methylcyclohexylglycines via chelated Kazmaier-Claisen rearrangement is described. These were shown to be potent scaffolds for the development of MMP inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Glycine / analogs & derivatives*
  • Glycine / chemical synthesis
  • Glycine / chemistry
  • Glycine / pharmacology
  • Humans
  • Matrix Metalloproteinase Inhibitors*
  • Molecular Conformation
  • Molecular Structure
  • Protease Inhibitors / chemical synthesis*
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / pharmacology

Substances

  • Matrix Metalloproteinase Inhibitors
  • Protease Inhibitors
  • Glycine