Synthesis and antibacterial activity of 1 beta-methylcarbapenems having a 2,2-disubstituted-1,3-diazabicyclo[3.3.0]octan-4-one moiety and related compounds. Part III

Abstract

The synthesis of new series of 1beta-methylcarbapenems having a 2,2-disubstituted-1,3-diazabicyclo[3.3.0]octan- and -[4.3.0]nonan-4-one moiety is described. Their in vitro antibacterial activities against both Gram-positive and Gram-negative bacteria were tested and the effect of the substituent of the bicyclic ring was investigated. A particular compound (16f) bearing a hydroxymethyl group showed the most potent antibacterial activity and the compound (17a) with a 1,3-diazabicyclo[4.3.0]nonane moiety exhibited excellent stability against renal dehydropeptidase-I (DHP-I) to Meropenem.