Synthesis and antibacterial activity of new 1β-methylcarbapenems having the potential for intramolecular nonbonded S···O interactions

Abstract

Mercaptoacetyliminothiadiazoline derivatives (19, 20) useful for the pendant moiety of 1β-methylcarbapenem antibiotics were efficiently synthesized. Acetyl derivative (18) of 20 was submitted to X-ray analysis, and a significant nonbonded S···O close contact was recognized in the crystallographic structure. New 1β-methylcarbapenems (5, 6) were synthesized by exploiting 19 and 20, and exhibited considerable antibacterial activities in vitro.