Synthesis and modification of a novel 1 beta-methyl carbapenem antibiotic, S-4661.
We describe an efficient method for introducing a sulfamoylamino group into the C-2' position of pyrrolidine using the Mitsunobu reaction. S-4661, its N-methyl analogues and stereoisomers were synthesized using this method and their structure-activity relationships were investigated.
Iso
Y
Y
Shionogi Research Laboratories, Shionogi & Co., Ltd., Osaka, Japan.
Irie
T
T
Iwaki
T
T
Kii
M
M
Sendo
Y
Y
Motokawa
K
K
Nishitani
Y
Y
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015780:Carbapenems / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000077726:Doripenem; D008826:Microbial Sensitivity Tests; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D015780:Carbapenems; D000077726:Doripenem