Synthesis and antibacterial activity of new 1beta-methylcarbapenems having the potential for intramolecular nonbonded S...O interactions.
Mercaptoacetyliminothiadiazoline derivatives (19, 20) useful for the pendant moiety of 1beta-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 1beta-methylcarbapenems (5, 6) were synthesized by exploiting 19 and 20, and exhibited considerable antibacterial activities in vitro.
Nagao
Y
Y
Faculty of Pharmaceutical Sciences, The University of Tokushima, Japan. ynagao@ph2.tokushima-u.ac.jp
Iimori
H
H
Nam
K H
KH
Sano
S
S
Shiro
M
M
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001419:Bacteria / Q000187:drug effects; D015780:Carbapenems / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008826:Microbial Sensitivity Tests; D010100:Oxygen / Q000737:chemistry; D013455:Sulfur / Q000737:chemistry
D000900:Anti-Bacterial Agents; D015780:Carbapenems; D013455:Sulfur; D010100:Oxygen