6-O-tert-butyl 1-O-methyl (8S)-8-(chloromethyl)-4-hydroxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylate | 176685-42-0

• 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: 6-O-tert-butyl 1-O-methyl (8S)-8-(chloromethyl)-4-hydroxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylate
• CAS: 176685-42-0
• 化学式: C₁₈H₂₁ClN₂O₅
• 分子量: 380.828
• InChiKey: UMMFSNRIDXLUMX-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  91.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-O-tert-butyl 1-O-methyl (8S)-8-(chloromethyl)-4-hydroxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylate 在 盐酸 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (8S)-6-[5-(1-benzofuran-2-carbonylamino)-1H-indole-2-carbonyl]-8-(chloromethyl)-4-hydroxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Various Structural Types of Novel Cyclopropapyrroloindole(CPI) Derivatives

  摘要：

  The various structural types of novel cyclopropapyrroloindole(CPI) derivatives (7 similar to 10) were synthesized and their cytotoxicity was evaluated. Among these derivatives, 3-methoxycarbonylCPI(3-MCCPI) derivatives (8a,b) and cyclopropapyrrolocarbazole (CPC) derivative (10a) were found to exhibit comparable cytotoxicity to U-73,975 (adozelesin) (1).

  DOI：

  10.3987/com-98-s21
• 作为产物：
  描述：

  6-O-tert-butyl 1-O-methyl (8S)-8-(chloromethyl)-4-phenylmethoxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylate 在 palladium on activated charcoal 甲酸铵 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到6-O-tert-butyl 1-O-methyl (8S)-8-(chloromethyl)-4-hydroxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylate
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Various Structural Types of Novel Cyclopropapyrroloindole(CPI) Derivatives

  摘要：

  The various structural types of novel cyclopropapyrroloindole(CPI) derivatives (7 similar to 10) were synthesized and their cytotoxicity was evaluated. Among these derivatives, 3-methoxycarbonylCPI(3-MCCPI) derivatives (8a,b) and cyclopropapyrrolocarbazole (CPC) derivative (10a) were found to exhibit comparable cytotoxicity to U-73,975 (adozelesin) (1).

  DOI：

  10.3987/com-98-s21

文献信息

• The novel cyclopropapyrroloindole(CPI) bisalkylators bearing 3,3′-(1,4-phenylene)diacryloyl group as a linker
  作者：Yasumichi Fukuda、Shigeki Seto、Hirosuke Furuta、Hiroyuki Ebisu、Yasuo Oomori、Shiro Terashima

  DOI：10.1016/s0960-894x(98)00346-1

  日期：1998.8

  The novel cyclopropapyrroloindole(CPI) bisalkylators were synthesized and their antitumor activity was evaluated. Among these derivatives, AT-760 (5a) in which the two 3-methoxycarbonyl-2-trifluoromethylCPI (MCTFCPI) moieties are connected with a 3,3'-(1,4-phenylene)diacryloyl group, was found to exhibit more prominent cytotoxicity and antitumor activity than U-77,779 (bizelesin) (1). (C) 1998 Elsevier Science Ltd. All rights reserved.