• Title/Summary/Keyword: pivaloyoxymethy esters

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Synthesis and Antibacterial Activities of New Oral Cephalosporins (새로운 경구용 세파로스포린의 합성 및 항균작용)

  • 나성범;정명희;김완주;지웅길
    • YAKHAK HOEJI
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    • v.37 no.3
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    • pp.295-305
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    • 1993
  • In order to develop oral cephalosporin having a new substituent at 3 position, the synthesis of cephalosporins modified at C-3 and the effect of the substituents on the oral absorption is studied. 7-[(Z)-2-(2-Aminothiazole- 4-yl)-2-methoxyiminoacetamidol-3-[4-(2-pyridyl )piperazinyl] thiocarbonylthiomethyl-3-cephem-4-carboxylic acid (CEN1) and 7-[(Z)-2-(2-aminothiazole-4-yl)-2-methoxyiminoacetamido]-3-[4-(2-pyrimid yl)piperazinylthiocarbonylthiomethyl-3-cephem-4-carboxylic acid (CEN2) were synthesized from 4-(2-piridyl)piperazinyl dithiocarbamate potassium salt or 4-(2-pirimidyl)piperazinyl dithiocarbamate potassium salt and cefotaxime. Also pivaloyloxymethyl esters of CEN1 and CEN2, pivaloyloxymethyl 7-[(Z)-2-(2-aminothiazole-4-yl)-2-methoxyiminoacetamido]-3-[4-(2-pyridyl )piperazinyllthiocarbonylthiomethyl-3-cephem-4-carboxylate (CENIP) and pivaloyloxymethyl 7-[(Z)-2-(2-aminothiazole-4-yl)-2-methoxyiminoacetamidol-3- [4-(2-pyrimid yl)piperazinyllthiocarbonylthiomethyl-3-cephem-4-carboxylate (CEN2P) were synthesized. The in vitro activities of two new oral cephalosporins, CEN1 and CEN2, were compared with the in vitro activities of cefaclor and cefotaxime against a variety of bacterial species. CEN2 has a broad antibacterial spectrum covering Gram-positive and Gram-negative bacteria, similar to that exhibited by CEN1 and cefotaxime. CEN1 and CEN2 were more active in vitro than cefaclor against Streptococcus pyogenes, Klebsiella aerogenes and Enterobacter cloacae.

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