benzhydryl 7β-(2-phenoxyacetamido)-3-(1,2,4-triazol-3-yl)thio-3-cephem-4-carboxylate | 308121-47-3

• 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: benzhydryl 7β-(2-phenoxyacetamido)-3-(1,2,4-triazol-3-yl)thio-3-cephem-4-carboxylate
• CAS: 308121-47-3
• 化学式: C₃₀H₂₅N₅O₅S₂
• 分子量: 599.691
• InChiKey: XXKWZJSZMMYWEP-UFHPHHKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  126.51
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  benzhydryl 7β-(2-phenoxyacetamido)-3-(1,2,4-triazol-3-yl)thio-3-cephem-4-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 、 苯甲醚 为溶剂， 反应 1.0h， 以41%的产率得到(6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-3-(4H-[1,2,4]triazol-3-ylsulfanyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  studies on anti-helicobacter pylori agents. part 2: new cephem derivatives

  摘要：

  The synthesis and optimization of the anti-Helicobacter pylori activity of a novel series of cephem derivatives are described. Introduction of thio-heterocyclic groups containing N- and S-atoms to the 3-position and phenyl or thienyl acetamido groups to the 7-position of the cephem nucleus dramatically improved the activity. From this series of derivatives, compound 13i was Found to have extremely potent in vitro anti-H. pylori activity, superior therapeutic efficacy compared to AMPC and CAM, no cross-resistance between CAM or MNZ and low potential for causing diarrhea due to instability to beta-lactamase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00163-2
• 作为产物：
  描述：

  苯氧乙酸 在 五氯化磷 、 N-三甲基硅基乙酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 benzhydryl 7β-(2-phenoxyacetamido)-3-(1,2,4-triazol-3-yl)thio-3-cephem-4-carboxylate
  参考文献：
  名称：

  studies on anti-helicobacter pylori agents. part 2: new cephem derivatives

  摘要：

  The synthesis and optimization of the anti-Helicobacter pylori activity of a novel series of cephem derivatives are described. Introduction of thio-heterocyclic groups containing N- and S-atoms to the 3-position and phenyl or thienyl acetamido groups to the 7-position of the cephem nucleus dramatically improved the activity. From this series of derivatives, compound 13i was Found to have extremely potent in vitro anti-H. pylori activity, superior therapeutic efficacy compared to AMPC and CAM, no cross-resistance between CAM or MNZ and low potential for causing diarrhea due to instability to beta-lactamase. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00163-2