(6R,7R)-3-(acetoxymethyl)-7-benzamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 2623-21-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6R,7R)-3-(acetoxymethyl)-7-benzamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 英文别名: (6R,7R)-3-(acetyloxymethyl)-7-benzamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 2623-21-4
• 化学式: C₁₇H₁₆N₂O₆S
• 分子量: 376.39
• InChiKey: JEWHISMKBZQDSL-MLGOLLRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (6R,7R)-3-(acetoxymethyl)-7-benzamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 在 吡啶 、 indium 、 三甲基氯硅烷 、 potassium iodide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 27.0h， 生成 3-methyl-7β-phenylacetamidoceph-3-em-4-carboxylic acid
  参考文献：
  名称：

  A facile synthesis of 7-amino-3-desacetoxycephalosporanic acid derivatives by indium-mediated reduction of 3-iodomethylcephems in aqueous media

  摘要：

  An efficient reductive conversion of 3-iodomethylcephalosporin and 3-acetoxymethylcephalosporin derivatives mediated by indium into the corresponding 3-methylcephems and 3-methylenecephams in moderate to good yields has been developed in an aqueous system. 3-Methylenecephams are converted into the corresponding 3-methylcephems under previously reported basic conditions quantitatively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00512-8
• 作为产物：
  描述：

  苯甲酰氯 、 7-氨基头孢烷酸 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以55%的产率得到(6R,7R)-3-(acetoxymethyl)-7-benzamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Exploitation of Antibiotic Resistance as a Novel Drug Target: Development of a β-Lactamase-Activated Antibacterial Prodrug

  摘要：

  Expression of beta-lactamase is the single most prevalent determinant of antibiotic resistance, rendering bacteria resistant to beta-lactam antibiotics. In this article, we describe the development of an antibiotic prodrug that combines ciprofloxacin with a beta-lactamase-cleavable motif. The prodrug is only bactericidal after activation by beta-lactamase. Bactericidal activity comparable to ciprofloxacin is demonstrated against clinically relevant E. coli isolates expressing diverse beta-lactamases; bactericidal activity was not observed in strains without beta-lactamase. These findings demonstrate that it is possible to exploit antibiotic resistance to selectively target beta-lactamase-producing bacteria using our prodrug approach, without adversely affecting bacteria that do not produce beta-lactamase. This paves the way for selective targeting of drug-resistant pathogens without disrupting or selecting for resistance within the microbiota, reducing the rate of secondary infections and subsequent antibiotic use.

  DOI：

  10.1021/acs.jmedchem.8b01923

文献信息

• The Chemistry of Cephalosporins. IV. Acetoxyl Replacements with Xanthates and Dithiocarbamates
  作者：Earle Van Heyningen、Carter N. Brown

  DOI：10.1021/jm00326a007

  日期：1965.3
• Buckwell, Stephen C.; Page, Michael I.; Longridge, Jethro L., Journal of the Chemical Society. Perkin transactions II, 1988, p. 1823 - 1828
  作者：Buckwell, Stephen C.、Page, Michael I.、Longridge, Jethro L.、Waley, Stephen G.

  DOI：——

  日期：——
• US4098999A
  申请人：——

  公开号：US4098999A

  公开（公告）日：1978-07-04