(Z)-benzhydryl 7β-[2-(2-allylthioethenylthio)acetamido]-3-(1,2,4-triazol-3-yl)thio-3-cephem-4-carboxylate | 308121-48-4

• 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: (Z)-benzhydryl 7β-[2-(2-allylthioethenylthio)acetamido]-3-(1,2,4-triazol-3-yl)thio-3-cephem-4-carboxylate
• CAS: 308121-48-4
• 化学式: C₂₉H₂₇N₅O₄S₄
• 分子量: 637.828
• InChiKey: KRIZDUNBVWHLDJ-GDOMVYHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  42.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  117.28
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (Z)-benzhydryl 7β-[2-(2-allylthioethenylthio)acetamido]-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55%的产率得到(Z)-7β-[2-(2-allylthioethenylthio)acetamido]-3-(1,2,4-triazol-3-yl)thio-3-cephem-4-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：

  benzhydryl 7β-formamido-3-(1,2,4-triazol-3-yl)thio-3-cephem-4-carboxylate 在 盐酸 、 N-三甲基硅基乙酰胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 (Z)-benzhydryl 7β-[2-(2-allylthioethenylthio)acetamido]-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