(S)-5-Acetyl-8-chloromethyl-4-hydroxy-6-[(E)-3-(4-methoxy-phenyl)-acryloyl]-2-methyl-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-1-carboxylic acid methyl ester | 205051-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-5-Acetyl-8-chloromethyl-4-hydroxy-6-[(E)-3-(4-methoxy-phenyl)-acryloyl]-2-methyl-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-1-carboxylic acid methyl ester
• CAS: 205051-29-2
• 化学式: C₂₆H₂₅ClN₂O₆
• 分子量: 496.947
• InChiKey: RSKNSTWCLYUALN-OJXHRBAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  108.93
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-5-Acetyl-8-chloromethyl-4-hydroxy-6-[(E)-3-(4-methoxy-phenyl)-acryloyl]-2-methyl-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-1-carboxylic acid methyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 1.33h， 以25%的产率得到
  参考文献：
  名称：

  Synthesis and antitumor activity of duocarmycin derivatives: modification at the C-7 position of segment-A of A-ring pyrrole compounds

  摘要：

  A series of the C7-substituted A-ring pyrrole derivatives of duocarmycin were synthesized, and evaluated for in vitro anticellular activity against HeLa S-3 cells and in vivo antitumor activity against murine sarcoma 180 in mice. All of the C7-substituted A-ring pyrrole compounds decreased potency in vitro and in vivo. However, some showed strong antitumor activity with T/C values less than 0.3. Among them, the 7-formyl compound 5d showed remarkable potent in vivo antitumor activity and low peripheral blood toxicity, which were equal to 2c. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00046-8
• 作为产物：
  描述：

  CPI 在 盐酸 、 三氟化硼乙醚 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 25.25h， 生成 (S)-5-Acetyl-8-chloromethyl-4-hydroxy-6-[(E)-3-(4-methoxy-phenyl)-acryloyl]-2-methyl-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and antitumor activity of duocarmycin derivatives: modification at the C-7 position of segment-A of A-ring pyrrole compounds

  摘要：

  A series of the C7-substituted A-ring pyrrole derivatives of duocarmycin were synthesized, and evaluated for in vitro anticellular activity against HeLa S-3 cells and in vivo antitumor activity against murine sarcoma 180 in mice. All of the C7-substituted A-ring pyrrole compounds decreased potency in vitro and in vivo. However, some showed strong antitumor activity with T/C values less than 0.3. Among them, the 7-formyl compound 5d showed remarkable potent in vivo antitumor activity and low peripheral blood toxicity, which were equal to 2c. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00046-8