MONOCYCLIC BETA-LACTAM INHIBITORS OF HUMAN-LEUKOCYTE ELASTASE - STEREOSPECIFIC SYNTHESIS AND ACTIVITY OF 3,4-DISUBSTITUTED-2-AZETIDINONES

Authors
SHAH SK FINKE PE BRAUSE KA CHANDLER GO ASHE BM WESTON H MAYCOCK AL MUMFORD RA DOHERTY JB
Citation
Sk. Shah et al., MONOCYCLIC BETA-LACTAM INHIBITORS OF HUMAN-LEUKOCYTE ELASTASE - STEREOSPECIFIC SYNTHESIS AND ACTIVITY OF 3,4-DISUBSTITUTED-2-AZETIDINONES, Bioorganic & medicinal chemistry letters, 3(11), 1993, pp. 2295-2298
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
3
Issue
11
Year of publication
1993
Pages
2295 - 2298
Database
ISI
SICI code
0960-894X(1993)3:11<2295:MBIOHE>2.0.ZU;2-E
Abstract
The synthesis of the four stereoisomers of -ethyl-4-[(4-carboxyphenyl) oxy]-1-[[(phenylmethyl) amino[carbonyl]-2-azetidinone (1) starting fro m either D or L-aspartic acid is reported. The trans (3R,4R) isomer 7a , prepared from L-aspartic acid had the most inhibitory activity again st human leukocyte elastase (HLE). This monocyclic beta-lactam was ver y resistant to hydrolysis and was found to be orally bioavailable in m armosets.