3-(5,6,7-trimethoxy-2-indole)acrylic acid | 287716-38-5

• 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: 3-(5,6,7-trimethoxy-2-indole)acrylic acid
• 英文别名: (E)-3-(5,6,7-trimethoxy-1H-indol-2-yl)prop-2-enoic acid
• CAS: 287716-38-5
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: RQELHGSQOVRVBL-SNAWJCMRSA-N

物化性质

• 沸点：
  494.3±40.0 °C(predicted)
• 密度：
  1.323±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  80.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(5,6,7-trimethoxy-2-indole)acrylic acid 在 2-氯-1-甲基吡啶碘化物 、 氢溴酸 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.34h， 生成
  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 氢氧化钾 、 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 22.83h， 生成 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

文献信息

• Synthesis and antitumor activity of duocarmycin derivatives: modification at the C-7 position of segment-A of A-ring pyrrole compounds
  作者：Nobuyoshi Amishiro、Akihiko Okamoto、Masami Okabe、Hiromitsu Saito

  DOI：10.1016/s0968-0896(00)00046-8

  日期：2000.5

  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.