Synthesis and antibacterial activity of 1beta-methylcarbapenems having a 2, 2-disubstituted-1, 3-diazabicyclo[3.3.0]octan-4-one moiety and related compounds. Part III.
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 (16 f) bearing a hydroxymethyl group showed the most potent antibacterial activity and the compound (17 a) with a 1, 3-diazabicyclo[4.3.0]nonane moiety exhibited excellent stability against renal dehydropeptidase-I (DHP-I) to Meropenem.
Oh
Chang-Hyun
CH
Medicinal Chemistry Research Center, Korea Institute of Science and Technology, Seoul, Korea.
Dong
Hyun-Gu
HG
Cho
Han-Won
HW
Park
Sung Jin
SJ
Hong
Joon Hee
JH
Baek
Daejin
D
Cho
Jung-Hyuck
JH
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D015780:Carbapenems / Q000138:chemical synthesis* / Q000494:pharmacology; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D007659:Ketones; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D015780:Carbapenems; D007659:Ketones