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Synthesis of a Masked p ‐Quinone Methide β ‐Lactam as an active metabolite of nocardicins
Author(s) -
Hakimelahi Gholam H.,
Tsay ShwuChen,
Hwu Jih Ru
Publication year - 1995
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19950780212
Subject(s) - chemistry , quinone methide , lactam , quinone , pyridinium , antimicrobial , in vitro , biological activity , metabolite , stereochemistry , in vivo , bacteria , biochemistry , organic chemistry , genetics , microbiology and biotechnology , biology
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.