β-(5',6',7'-trimethoxy-2'-indolyl)acryloyl 8-hydroxy 2-methyl-3-formyl-A-ring pyrrole duocarmycin C2 | 205051-19-0

• 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: β-(5',6',7'-trimethoxy-2'-indolyl)acryloyl 8-hydroxy 2-methyl-3-formyl-A-ring pyrrole duocarmycin C2
• 英文别名: (8S)-8-(chloromethyl)-4-hydroxy-2-methyl-6-[(E)-3-(5,6,7-trimethoxy-1H-indol-2-yl)prop-2-enoyl]-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carbaldehyde
• CAS: 205051-19-0
• 化学式: C₂₇H₂₆ClN₃O₆
• 分子量: 523.973
• InChiKey: HHSJASMUMIIWMR-LLYBFZRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  β-(5',6',7'-trimethoxy-2'-indolyl)acryloyl 8-hydroxy 2-methyl-3-formyl-A-ring pyrrole duocarmycin C2 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 0.67h， 以47%的产率得到β-(5',6',7'-trimethoxy-2'-indolyl)acryloyl 2-methyl-3-formyl-A-ring pyrrole duocarmycin
  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 盐酸 、 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 、 乙酸乙酯 、 甲苯 为溶剂， 反应 45.5h， 生成 β-(5',6',7'-trimethoxy-2'-indolyl)acryloyl 8-hydroxy 2-methyl-3-formyl-A-ring pyrrole duocarmycin C2
  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
  作者：Nobuyoshi Amishiro、Satoru Nagamura、Eiji Kobayashi、Akihiko Okamoto、Katsushige Gomi、Masami Okabe、Hiromitsu Saito

  DOI：10.1016/s0968-0896(00)00086-9

  日期：2000.7

  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.