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 |
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Authors: | Hakimelahi Gholam Hossein Li Pai-Chi Moosavi-Movahedi Ali A Chamani Jamshid Khodarahmi Ghadam Ali Ly Tai Wei Valiyev Famil Leong Max K Hakimelahi Shahram Shia Kak-Shan Chao Ito |
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Affiliation: | Institute of Chemistry, Academia Sinica, TaiGen Biotechnology, Taipei, Taiwan, R. O. C. hosein@taigenbiotech.com.tw |
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Abstract: | Racemic 7-(phenylacetamido)-1-dethia-3-aza-1-carba-2-oxacephem 3 was synthesized and found to possess antibacterial activity against Staphylococcus aureus FDA 209P, Escherichia coli ATCC 39188, Pseudomonas aeruginosa 1101-75 and Klebsiella pneumoniae NCTC 418 as well as the beta-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 beta-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. |
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