Studies on cephalosporin antibiotics. II. Synthesis, antibacterial activity and oral absorption of 3-alkoxycarbonylmethoxy-7.BETA.-((Z)-2-(2-aminothiazol-4-yl)-2-(O-substituted oxyimino)acetamido)cephalosporins.

Yokoo, Chihiro; Goi, Masami; Onodera, Akira; Murata, Mitsuo; Nagate, Takatoshi; Watanabe, Yoshiaki; Sota, Kaoru

doi:10.7164/antibiotics.41.181

Cited by 2 publications

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The Chemistry of 2‐Azetidinones (β‐Lactams)

Alcaide¹,

Almendros²,

Luna³

2011

Modern Heterocyclic Chemistry

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The large number of recent reports on b-lactam chemistry demonstrates the increasing interest in this important class of compounds. Monocyclic b-lactams frequently serve as precursors for the synthesis of classical bicyclic b-lactam antibiotics. The cyclic 2-azetidinone skeleton has been extensively used as a template on which to build the heterocyclic structure fused to the four-membered ring, using the chirality and functionalization of the b-lactam nucleus as a stereocontrolling element. The discovery of nonclassical b-lactam antibiotics, such as monobactams and nocardicins, coupled with ever-growing new applications such as enzyme inhibition has triggered a renewed interest in the building of new monocyclic b-lactam derivatives. Besides the utility of b-lactams as biologically active agents, they are used as intermediates in a-and b-amino acid synthesis, as well as building blocks for alkaloids, heterocycles, taxoids and other types of compounds of biological and medicinal interest. Physicochemical Data Computational ChemistryTheoretical studies show that b-lactams are weaker bases, in the gas phase, than acyclic amides [1]. The attenuation of basicity upon cyclization is stronger than that found for cyclic ketones of similar size due to the existence of a negative hyperconjugation effect that is present in b-lactams but not in cyclic ketones. Ab initio calculations indicate that both b-lactams and acyclic amides are oxygen bases, but the gap between the oxygen and nitrogen intrinsic basicities is much smaller in the former due to the aforementioned cyclization effects. This decrease of the oxygen Modern Heterocyclic Chemistry, First Edition. Edited

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The Chemistry of 2‐Azetidinones (β‐Lactams)

Alcaide¹,

Almendros²,

Luna³

2011

Modern Heterocyclic Chemistry

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Studies on cephalosporin antibiotics. VI. Synthesis, antibacterial activity and oral efficacy in mice of new 7.BETA.-((Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino)-acetamido)-3-(substituted alkylthio)cephalosporins.

et al. 1992

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A series of new 7j?-[(Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetamido]cephalosporins(1) having various substituted alkylthio groups at the C-3 position of the cephemnucleus were prepared and evaluated for antibacterial activity and oral absorption in rats. Of these, the cephalosporin with a cyanomethylthio group (la) showed the greatest activity against Staphylococcus aureus andGram-negative bacteria. Its pivaloyloxymethyl ester (6a), a representative prodrug, exhibited good in vivo efficacy in mice by oral administration. The structure-activity relationships of 1 are also presented.

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Studies on cephalosporin antibiotics. II. Synthesis, antibacterial activity and oral absorption of 3-alkoxycarbonylmethoxy-7.BETA.-((Z)-2-(2-aminothiazol-4-yl)-2-(O-substituted oxyimino)acetamido)cephalosporins.

Cited by 2 publications

References 4 publications

The Chemistry of 2‐Azetidinones (β‐Lactams)

The Chemistry of 2‐Azetidinones (β‐Lactams)

Studies on cephalosporin antibiotics. VI. Synthesis, antibacterial activity and oral efficacy in mice of new 7.BETA.-((Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino)-acetamido)-3-(substituted alkylthio)cephalosporins.

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