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  • Title: Semisynthetic beta-lactam antibiotics. VI. Synthesis and antimicrobial activity of alpha-hydrazonobenzylcephalosporins.
    Author: Monguzzi R, Pinza M, Pifferi G, Visconti M, Broccali G.
    Journal: Farmaco Sci; 1985 Dec; 40(12):956-69. PubMed ID: 4092767.
    Abstract:
    Using as a model cephalosporins with an alpha-hydroxyimino moiety in the side chain, some new (E)-alpha-hydrazono and alpha-methylhydrazono benzyl cephalosporins were prepared. While the synthesis of methylhydrazono-derivatives (I a-d) involved direct condensation of the methylhydrazionacid (II a-b) with a protected 7-aminocephalosporanic derivative, the N-unsubstituted compounds (I e-f) had to be prepared from the N-acyl protected hydrazono acids (III a-d). The cephalosporin (I f) was also obtained as Z-isomer by condensation of the corresponding alpha-oxo compound with 4-nitrobenzyloxycarbonylhydrazine, chromatographic separation of the obtained E-Z mixture, and hydrogenolysis of the Z form. The in vitro antibacterial evaluation showed that N-methyl substitution is favorable among the E compounds, whereas among the N-unsubstituted hydrazono derivatives, the compound Z-(I f), although less stable, is much more potent than the corresponding E-isomer.
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