The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF CARBAPENEMS RELATED TO C-19393 H2
HIDEAKI NATSUGARIYOSHIHIRO MATSUSHITANORIKAZU TAMURAKOUICHI YOSHIOKAMASAHIRO KONDOKENJI OKONOGIMITSUZO KUNOMICHIHIKO OCHIAI
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1983 Volume 36 Issue 7 Pages 855-875

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Abstract

By applying the synthetic process reported in our previous paper, we synthesized new carbapenems having various (substituted) thio and alkoxy groups at the C(3) position and 1-hydroxy-1-methylethyl and analogous groups at the C(6) position with cis- and trans-stereochemistry; the in vitro antibacterial and β-lactamase inhibitory activities of these new carbapenems were examined. Compared to C-19393 H2, some of these compounds (e.g., 11A-a-3-5) showed improved in vitro antibacterial activity especially against Pseudomonas aeruginosa; they showed a strong β-lactamase inhibitory activity as well. Two noteworthy effects of substituent variation at the C(6) position on the activities were observed: 1) the trans-configuration caused a definite loss; and 2) introduction of 1-hydroxycyclobutyl and 1-hydroxy-1-methylpropyl groups in place of the 1-hydroxy-1-methylethyl group caused a diminution. The carbapenem (13A-a-2)with an alkoxy group at the C(3) position had a marked decrease in activity compared to the corresponding thio-substituted carbapenem (11A-a-12).

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