Isfahan University of Medical Sciences

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Application of the Barton Photochemical Reaction in the Synthesis of 1-Dethia-3-Aza-1-Carba-2-Oxacephem: A Novel Agent Against Resistant Pathogenic Microorganisms Publisher Pubmed



Hakimelahi GH1, 2 ; Li PC1 ; Moosavimovahedi AA3 ; Chamani J3 ; Khodarahmi GA4 ; Ly TW1 ; Valiyev F1 ; Leong MK2 ; Hakimelahi S1 ; Shia KS2 ; Chao I1
Authors

Source: Organic and Biomolecular Chemistry Published:2003


Abstract

Racemic 7-(phenylacetamido)-1-dethia-3-aza-1-carba-2-oxacephem 3 was synthesized and found to possess antibacterial activity against Staphylococcus aureus PDA 209P, Escherichia coli ATCC 39188, Pseudomonas aeruginosa 1101-75 and Klebsiella pneumoniae NCTC 418 as well as the β-lactamase producing organisms E. coli A9675 and P. aeruginosa 18S-H and the methicillin-resistant organism S. aureus 95. Formation of the carbacephem 3 originated from the Barton photochemical reaction in the conversion of 8 to 10. Intramolecular cyclization of syn-oximino β-lactam 10 afforded 7-azido-2-oxa-3-azacephem 11, which was reduced and acylated to 12. Enzymatic removal of the methyl group from 12 gave the target molecule 3.