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Synthesis and Stability of Functionalized Epoxides Topologically Related To Beta-lactam Antibiotics

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Marchand-Brynaert, Jacqueline [UCL] Ferroud, Didier Serckx-Poncin, Béatrice [UCL] Ghosez, Léon [UCL]

Epoxides 3-4 topologically related to penicillins and oxamazins have been designed as potential alkylating inhibitors of bacterial D, D-peptidases. A series of N-acylated olefins 17-19 and 22 have been prepared. It was found that the corresponding epoxides bearing a free carboxyl group were unstable. Neither the olefinic precursors nor the lactones 23 resulting from ring opening of the epoxides 4 exhibited any antibacterial activity.

Document type Article de périodique (Journal article) – Article de recherche
Publication date 1990
Language Anglais
Journal information "Societes Chimiques Belges. Bulletin" - Vol. 99, no. 11-12, p. 1075-1084 (1990)
Peer reviewed yes
Publisher Soc Chimique Belgique (Brussels)
issn 0037-9646
Publication status Publié
Affiliation UCL - SC/CHIM - Département de chimie
Links
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Bibliographic reference Marchand-Brynaert, Jacqueline ; Ferroud, Didier ; Serckx-Poncin, Béatrice ; Ghosez, Léon. Synthesis and Stability of Functionalized Epoxides Topologically Related To Beta-lactam Antibiotics. In: Societes Chimiques Belges. Bulletin, Vol. 99, no. 11-12, p. 1075-1084 (1990)
Permanent URL http://hdl.handle.net/2078.1/51475