(7S,6R)-7-(2-thienylacetamido)-3-carbomethoxy-1-carba-1-dethia-3-cephem-4-carboxylic acid | 114711-19-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (7S,6R)-7-(2-thienylacetamido)-3-carbomethoxy-1-carba-1-dethia-3-cephem-4-carboxylic acid
• 英文别名: (6R,7S)-3-methoxycarbonyl-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 114711-19-2
• 化学式: C₁₆H₁₆N₂O₆S
• 分子量: 364.379
• InChiKey: COPNHZYUSBOOHU-PWSUYJOCSA-N

物化性质

• 沸点：
  686.9±55.0 °C(predicted)
• 密度：
  1.52±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate 在 2,6-二甲基吡啶 、 盐酸 、 双(乙腈)氯化钯(II) 、 五氯化磷 、 三乙胺 、 lithium chloride 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 (7S,6R)-7-(2-thienylacetamido)-3-carbomethoxy-1-carba-1-dethia-3-cephem-4-carboxylic acid
  参考文献：
  名称：

  Comparative reactivity of 1-carba-1-dethiacephalosporins with cephalosporins

  摘要：

  Nine matched pairs of cephalosporins and their 1-carba-1-dethiacephalosporin analogues have been compared with regard to microbiological activity, beta-lactam carbonyl infrared absorption, and aqueous stability. In general the microbiological activity of the pairs of compounds were very similar across a broad range of bacteria. The infrared absorption bands for the beta-lactam carbonyls of the pairs indicated a general trend for the 1-carba-1-dethiacephalosporins to absorb at lower frequencies than the corresponding cephalosporins. All of the 1-carba-1-dethiacephalosporins did however present a striking stability enhancement over their cephalosporin counterparts at pH = 10 or 11 in water. This marked contrast of MIC similarity with the observed differences in chemical reactivity clearly demonstrates hydroxide ion catalyzed hydrolysis is not a good model for transpeptidase activity unless the compounds comprise a limited domain of structural type.

  DOI：

  10.1021/jm00168a019

文献信息

• 1-Carbacephalosporin antibiotics
  申请人：ELI LILLY AND COMPANY

  公开号：EP0232623A1

  公开（公告）日：1987-08-19

  7β-Acylamino-3-alkoxycarbonyl-(and 3-keto)-1-carba (1-dethia)-3-cephem-4-carboxylic acids and derivatives and related 3-substituted compounds are provided as antibiotics useful for treating infections in man and other animals. Pharmaceutical formulations comprising the antibiotics, intermediates, and a process for their preparation are also provided.

  本发明提供了 7β-乙酰氨基-3-烷氧基羰基-（和 3-酮基）-1-咔巴（1-二硫杂）-3-头孢-4-羧酸及其衍生物和相关的 3-取代化合物，作为抗生素可用于治疗人类和其他动物的感染。此外，还提供了包含这些抗生素、中间体及其制备工艺的药物制剂。
• MUNROE, JOHN E.
  作者：MUNROE, JOHN E.

  DOI：——

  日期：——
• US4892942A
  申请人：——

  公开号：US4892942A

  公开（公告）日：1990-01-09
• Comparative reactivity of 1-carba-1-dethiacephalosporins with cephalosporins
  作者：Larry C. Blaszczak、Raymond F. Brown、Gwendolyn K. Cook、William J. Hornback、Joseph M. Indelicato、Chris L. Jordan、Alan S. Katner、Michael D. Kinnick、John H. McDonald

  DOI：10.1021/jm00168a019

  日期：1990.6

  Nine matched pairs of cephalosporins and their 1-carba-1-dethiacephalosporin analogues have been compared with regard to microbiological activity, beta-lactam carbonyl infrared absorption, and aqueous stability. In general the microbiological activity of the pairs of compounds were very similar across a broad range of bacteria. The infrared absorption bands for the beta-lactam carbonyls of the pairs indicated a general trend for the 1-carba-1-dethiacephalosporins to absorb at lower frequencies than the corresponding cephalosporins. All of the 1-carba-1-dethiacephalosporins did however present a striking stability enhancement over their cephalosporin counterparts at pH = 10 or 11 in water. This marked contrast of MIC similarity with the observed differences in chemical reactivity clearly demonstrates hydroxide ion catalyzed hydrolysis is not a good model for transpeptidase activity unless the compounds comprise a limited domain of structural type.