Design and synthesis of bridged $gamma;-lactams as analogues of $beta;-lactam antibiotics

Bioorganic & Medicinal Chemistry Letters
2004.0

Abstract

Anti-Bredt bridged bicyclo[3.2.1] gamma-lactams were designed as inhibitors of penicillin binding proteins (PBPs). The compounds were prepared by a carbenoid insertion into a lactam N-H bond. Their weak antibacterial activity could either be explained by a poor chemical stability or by unfavorable steric interactions of the methylene bridge of the gamma-lactam with the targeted enzymes.

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