Synthesis and .beta.-lactamase inhibitory properties of 2.beta.-(chloromethyl)-2.alpha.-methylpenam-3.alpha.-carboxylic acid 1,1-dioxide
- 1 December 1981
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 24 (12) , 1531-1534
- https://doi.org/10.1021/jm00144a034
Abstract
Potassium 2.beta.-(chloromethyl)-2.alpha.-methylpenam-3.alpha.-carboxylate 1,1-dioxide (BL-P2013) and its pivaloyloxymethyl ester were prepared by the conversion of 6-aminopenicillanic acid to p-nitrobenzyl 6.alpha.-bromo-2,2-dimethylpenam-3.alpha.-carboxylate 1-oxide, which was rearranged with benzoyl chloride and quinoline to p-nitrobenzyl 6.alpha.-bromo-2.beta.-(chloromethyl)-2.alpha.-methylpenam-3.alpha.-carboxylate in 65% yield. Oxidation and catalytic hydrogenation afforded BL-P2013, which is a potent inhibitor of various bacterial .beta.-lactamases and protects amoxicillin from .beta.-lactamases in in vitro and in vivo systems.This publication has 4 references indexed in Scilit:
- 6 β-Bromopenicillanic acid inactivates β-lactamase IBiochemical Journal, 1979
- CP-45,899, a Beta-Lactamase Inhibitor That Extends the Antibacterial Spectrum of Beta-Lactams: Initial Bacteriological CharacterizationAntimicrobial Agents and Chemotherapy, 1978
- A sulfone .BETA.-lactam compound which acts as a .BETA.-lactamase inhibitor.The Journal of Antibiotics, 1978
- Clavulanic Acid: a Beta-Lactamase-Inhibiting Beta-Lactam from Streptomyces clavuligerusAntimicrobial Agents and Chemotherapy, 1977