erthyl 3-(5,6,7-trimethoxy-2-indolyl)acrylate | 297137-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: erthyl 3-(5,6,7-trimethoxy-2-indolyl)acrylate
• CAS: 297137-26-9
• 化学式: C₁₆H₁₉NO₅
• 分子量: 305.331
• InChiKey: OYKRFEBHGIAJLR-VOTSOKGWSA-N

物化性质

• 沸点：
  472.7±40.0 °C(predicted)
• 密度：
  1.214±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.78
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  erthyl 3-(5,6,7-trimethoxy-2-indolyl)acrylate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以99%的产率得到3-(5,6,7-trimethoxy-2-indole)acrylic acid
  参考文献：
  名称：

  Synthesis and antitumor activity of duocarmycin derivatives

  摘要：

  A series of A-ring pyrrole derivatives of duocarmycin bearing beta-(5',6',7'-trimethoxy-2'-indolyl)acryloyl group were synthesized, and evaluated for in vitro anticellular activity against HeLa Sg cells and in vivo antitumor activity against murine sarcoma 180 in mice. New Seg-B analogues bearing beta-(5',6',7'-trimethoxy-2'-indolyl)acryloyl group containing double bond as spacer had lower peripheral blood toxicity than the derivatives bearing S',6',7'-trimethoxyindole-2'-carboxyl group in Seg-B of the natural type. Moreover, most of them exhibited potent antitumor activity against in vivo murine tumor models. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00086-9
• 作为产物：
  描述：

  3-methoxycarbonyl-2-methylduocarmycin A 在 chromium trioxide-pyridine complex 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 21.33h， 生成 erthyl 3-(5,6,7-trimethoxy-2-indolyl)acrylate
  参考文献：
  名称：

  Synthesis and antitumor activity of duocarmycin derivatives

  摘要：

  A series of A-ring pyrrole derivatives of duocarmycin bearing beta-(5',6',7'-trimethoxy-2'-indolyl)acryloyl group were synthesized, and evaluated for in vitro anticellular activity against HeLa Sg cells and in vivo antitumor activity against murine sarcoma 180 in mice. New Seg-B analogues bearing beta-(5',6',7'-trimethoxy-2'-indolyl)acryloyl group containing double bond as spacer had lower peripheral blood toxicity than the derivatives bearing S',6',7'-trimethoxyindole-2'-carboxyl group in Seg-B of the natural type. Moreover, most of them exhibited potent antitumor activity against in vivo murine tumor models. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00086-9