Structure-activity relationships in the 2-arylcarbapenem series. Synthesis of 1-methyl-2-arylcarbapenems

• Published in: Journal of medicinal chemistry Vol. 30; no. 5; pp. 871 - 880
• Main Authors: Guthikonda, Ravindra Nath, Cama, L. D, Quesada, M, Woods, M. F, Salzmann, T. N, Christensen, B. G
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01.05.1987
• Subjects: Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - pharmacology; Bacteria - drug effects; Chemical Phenomena; Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Organic chemistry; Preparations and properties; Structure-Activity Relationship; Thienamycins - pharmacology; Four membered ring; Structure activity relation; Angular nitrogen heterocycle; Nitrogen heterocycle; Silicon Organic compounds; Lactam; Bicyclic compound; Antimicrobial agent
• ISSN: 0022-2623; 1520-4804
• DOI: 10.1021/jm00388a022

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.