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

Marchand-Brynaert, Jacqueline;Ferroud, Didier;Serckx-Poncin, Béatrice;Ghosez, Léon
(1990) Societes Chimiques Belges. Bulletin — Vol. 99, n° 11-12, p. 1075-1084 (1990)

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  • Marchand-Brynaert, JacquelineUCLouvain
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  • Ferroud, Didier
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  • Serckx-Poncin, BéatriceUCLouvain
    Author
  • Ghosez, LéonUCLouvain
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Abstract
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.
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Marchand-Brynaert, J., Ferroud, D., Serckx-Poncin, B., & Ghosez, L. (1990). Synthesis and Stability of Functionalized Epoxides Topologically Related To Beta-lactam Antibiotics. Societes Chimiques Belges. Bulletin, 99(11-12), 1075-1084. https://doi.org/10.1002/bscb.19900991126 (Original work published 1990)