Stereoselective synthesis and antibacterial evaluation of 4-amido-isothiazolidinone oxides

Bioorg Med Chem Lett. 2001 Aug 20;11(16):2111-5. doi: 10.1016/s0960-894x(01)00409-7.

Abstract

Two well-defined oxidative chlorination-cyclization processes have been developed for the stereoselective synthesis of a variety of 4-amido-isothiazolidinone oxide derivatives. The stereochemistry of the cyclization products was confirmed by X-ray crystallography. These new compounds were designed as bacterial serine protease inhibitors. In tests, some of them showed weak antibacterial activity.

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amides / pharmacology
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Chlorine / chemistry
  • Cyclization
  • Enterobacter cloacae / drug effects
  • Klebsiella pneumoniae / drug effects
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Moraxella catarrhalis / drug effects
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry
  • Thiazoles / pharmacology

Substances

  • Amides
  • Anti-Bacterial Agents
  • Thiazoles
  • Chlorine