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Synthesis of a Masked p -Quinone Methide β -Lactam as an active metabolite of nocardicins (1995)

Hakimelahi, Gholam H. ; Tsay, Shwu-Chen ; Hwu, Jih Ru

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 78 (1995), S. 411-420

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Nocardicin A analogues 30, 34, and 38 as well as the highly strained quinone methide 43 were synthesized. β -Lactam 34 was found biologically active against several Gram-negative microorganisms in vitro; pyridinium N-oxide derivative 38 possessed activity against Gram-positive S. aureus bacterium. Masked p-quinone methide β -lactam 43 exhibited significant antimicrobial activity in vitro. A mechanism involving an oxidation in vivo is proposed for the unprecedented biological properties of nocardicins.

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19950780212

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