N-azamonobactams. 1. The synthesis of some 3-substituted N-azamonobactam derivatives.
Ring closure of the N-(tert-butyloxycarbonyl)-L-serine 2-(diphenylmethylene)hydrazide (10a) and the corresponding L-threonine derivative (10b) gave good yields of the beta-lactams 11a and 11b. Catalytic hydrogenation afforded the corresponding N-amino beta-lactams 12a and 12b. These compounds were then further transformed into 3-(S)-[[(2-amino-4-thiazolyl)-(Z)-(methoxyimino)acetyl]amino-2-oxo-1- azetidinyl]sulfamic acid analogs 18, 23, and 30a and 30b. None of these compounds exhibited any interesting biological activity.
Curran
W V
WV
Medical Research Division, American Cyanamid Company, Pearl River, New York 10965.
Ross
A A
AA
Lee
V J
VJ
D001398:Aztreonam / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D055598:Chemical Phenomena; D002621:Chemistry; D008826:Microbial Sensitivity Tests
D001398:Aztreonam