Structure-activity relationships in the 2-arylcarbapenem series: synthesis of 1-methyl-2-arylcarbapenems

J Med Chem. 1987 May;30(5):871-80. doi: 10.1021/jm00388a022.

Abstract

The labile tert-butyldimethylsilyl esters of the azetidinones 6-8b served as the crucial synthons in the preparation of the potentially useful ylide pyridyl thio esters 18-20. These intermediates were utilized to synthesize a host of title carbapenems 25-30d, 32, and 49-53. The antimicrobial properties and DHP-I susceptibility of these carbapenems were studied with reference to thienamycin.

Publication types

  • Comparative Study

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / pharmacology*
  • Bacteria / drug effects*
  • Chemical Phenomena
  • Chemistry
  • Structure-Activity Relationship
  • Thienamycins / pharmacology

Substances

  • Anti-Bacterial Agents
  • Thienamycins
  • thienamycin