Synthesis of reactive gamma-lactams related to penicillins and cephalosporins

Citation
Sh. Bhattia et al., Synthesis of reactive gamma-lactams related to penicillins and cephalosporins, J CHEM S P1, (17), 1999, pp. 2449-2454
Citations number
27
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
17
Year of publication
1999
Pages
2449 - 2454
Database
ISI
SICI code
0300-922X(1999):17<2449:SORGRT>2.0.ZU;2-O
Abstract
gamma-Lactams with structures analogous to both penicillin (1) and cephalos porin (2) antibiotics have been synthesised. These compounds show high reac tivity towards modest nucleophiles in keeping with their design as potentia l inhibitors of bacterial cell wall biosynthesis. Reactive gamma-lactam ana logues 27 and 29 of beta-lactamase inhibitors such as 22 have also been pre pared. An X-ray crystal structure of the cephalosporin analogue 8 has allow ed structural comparisons to be made with the classical beta-lactam antibio tic cephaloridine (30).