Synthesis and biological evaluation of an electronically activated isooxacephem

G H Hakimelahi; S C Tsay; H H Tso; Z Ramezani; J R Hwu

doi:10.1016/0968-0896(96)00131-9

Synthesis and biological evaluation of an electronically activated isooxacephem

Bioorg Med Chem. 1996 Aug;4(8):1361-4. doi: 10.1016/0968-0896(96)00131-9.

Authors

G H Hakimelahi¹, S C Tsay, H H Tso, Z Ramezani, J R Hwu

Affiliation

¹ Organosilicon and Synthesis Laboratory, Institute of Chemistry, Academia Sinica, Taipei, Taiwan, R.O.C.

PMID: 8879559
DOI: 10.1016/0968-0896(96)00131-9

Abstract

New isooxacephem (+/-)-3-ethyl 2-hydrogen (6RS,7RS)-8-oxo-7-(phenylacetamido)-4-oxa-1-azabicyclo [4.2.0]oct-2-ene-2, 3-dicarboxylate (8) was synthesized from (+/-)-dibenzyl 2-[cis-2-oxo-3-(phenylacetamido)-4-styryl-1-azetidinyl]-2-[t- butyldimethylsiloxy(methoxycarbonyl)methyl]malonate (1) in six steps. This bicyclic beta-lactam was found to possess notable biological activities against several pathogenic microorganisms in vitro, including Staphylococcus aureus 95, S. aureus FDA 209P, Escherichia coli ATCC 39188, Salmonella typhi O-901, Pseudomonas aeruginosa 18S-H, P. aeruginosa 1101-75, and Klebsiella pneumoniae NCTC 418. The electronic activation of the beta-lactam moiety by an ester group plays a prominent role in the biological activity of this novel isooxacephem.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemistry*
Cephalosporins / chemistry*
Microbial Sensitivity Tests
Pseudomonas aeruginosa / drug effects
Staphylococcus aureus / drug effects

Substances

Anti-Bacterial Agents
Cephalosporins
L 656575