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Synthesis of New C-6 Alkyliden Penicillin Derivatives as Beta-Lactamase Inhibitors

Synthesis of New C-6 Alkyliden Penicillin Derivatives as Beta-Lactamase Inhibitors

B Di Giacomo, G Tarzia, A Bedini, G Gatti, F Bartoccini, C Balsamini, A Tontini, W Baffone, E Di Modugno, A Felici

Farmaco. 2002 Apr;57(4):273-83.

PMID: 11989807

Abstract:

New penicillin, penicillin sulfone and sulfoxide derivatives bearing a C-6-alkyliden substituent were prepared. Their chemical synthesis, in vitro antibacterial activity and inhibition properties against two selected enzymes representing Class A and C beta-lactamases are reported. Compounds 3a-c, 7a-c were able to inhibit either TEM-1 (a Class A enzyme, from Escherichia coli) or P-99 (a Class C enzyme, from E. cloacae), or both enzymes, when tested in competition experiments using nitrocefin as the reporter substrate. However, when tested in combination with amoxicillin, the same compounds did not show synergistic effects against E. coli and E. cloacae strains producing TEM-1 and P99 enzymes, respectively. This finding is most likely related to poor penetration through the bacterial cell wall, as shown by using a more permeable isogenic E. coli strain. Interestingly, a synergistic effect against a strain of S. aureus which produces PC1-enzyme (a Class A beta-lactamase) was observed for compound 3a when used in combination with amoxicillin.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
CS3104571	Amoxicillin Related Compound C			Price

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