8-acetoxymethyl-4-benzyloxy-6-t-butoxycarbonyl-1,2,3,6,7,8-hexahydro-1,2-dioxobenzo<1,2-b;4,3-b'>dipyrrole | 132628-62-7

• 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: 8-acetoxymethyl-4-benzyloxy-6-t-butoxycarbonyl-1,2,3,6,7,8-hexahydro-1,2-dioxobenzo<1,2-b;4,3-b'>dipyrrole
• 英文别名: isatin；tert-butyl 8-(acetyloxymethyl)-1,2-dioxo-4-phenylmethoxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-6-carboxylate
• CAS: 132628-62-7
• 化学式: C₂₅H₂₆N₂O₇
• 分子量: 466.491
• InChiKey: XKBPHEGPYCEZDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-acetoxymethyl-4-benzyloxy-6-t-butoxycarbonyl-1,2,3,6,7,8-hexahydro-1,2-dioxobenzo<1,2-b;4,3-b'>dipyrrole 在 咪唑 、 碳酸氢钠 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成
  参考文献：
  名称：

  First total synthesis of dl-duocarmycin A

  摘要：

  DOI：

  10.1016/s0040-4039(00)97151-x
• 作为产物：
  描述：

  3-acetoxymethyl-5-amino-6-benzyloxy-1-t-butoxycarbonyl-2,3-dihydro-1H-indole 在 磺酰氯 、 1,8-双二甲氨基萘 、 溶剂黄146 、 三乙胺 、 copper(II) oxide 、 copper dichloride 作用下， 以 丙酮 为溶剂， 反应 29.33h， 生成 8-acetoxymethyl-4-benzyloxy-6-t-butoxycarbonyl-1,2,3,6,7,8-hexahydro-1,2-dioxobenzo<1,2-b;4,3-b'>dipyrrole
  参考文献：
  名称：

  Synthetic studies on duocarmycin. 1. Total synthesis of dl-duocarmycin A and its 2-epimer

  摘要：

  The title synthesis was first achieved by employing novel methoxycarbonylation of the C-4-position of the 5-aminoindoline by way of the isatin and subsequent Dieckmann cyclization to the methyl 2-methylindoxyl-2- carboxylate as key steps. In vitro cytotoxicity assay against P388 murine leukemia obviously disclosed that cytotoxicities of the synthesized compounds are comparable and almost half of that of natural (+)-duocarmycin A.

  DOI：

  10.1016/s0040-4020(01)86993-3

文献信息

• Synthesis and Cytotoxicity of Various Structural Types of Novel Cyclopropapyrroloindole(CPI) Derivatives
  作者：Yasumichi Fukuda、Hirosuke Furuta、Yoshie Kusama、Hiroyuki Ebisu、Yasuo Oomori、Shiro Terashima

  DOI：10.3987/com-98-s21

  日期：——

  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).
• First total synthesis of dl-duocarmycin A
  作者：Yasumichi Fukuda、Kazuhiko Nakatani、Yoshio Ito、Shiro Terashima

  DOI：10.1016/s0040-4039(00)97151-x

  日期：1990.1
• FUKUDA, YASUMICHI;NAKATANI, KAZUHIKO;ITO, YOSHIO;TERASHIMA, SHIRO, TETRAHEDRON LETT., 31,(1990) N6, C. 6699-6702
  作者：FUKUDA, YASUMICHI、NAKATANI, KAZUHIKO、ITO, YOSHIO、TERASHIMA, SHIRO

  DOI：——

  日期：——
• JPH04117383A
  申请人：——

  公开号：JPH04117383A

  公开（公告）日：1992-04-17
• Synthetic studies on duocarmycin. 1. Total synthesis of dl-duocarmycin A and its 2-epimer
  作者：Yasumichi Fukuda、Yoshio Itoh、Kazuhiko Nakatani、Terashima Shiro

  DOI：10.1016/s0040-4020(01)86993-3

  日期：1994.2

  The title synthesis was first achieved by employing novel methoxycarbonylation of the C-4-position of the 5-aminoindoline by way of the isatin and subsequent Dieckmann cyclization to the methyl 2-methylindoxyl-2- carboxylate as key steps. In vitro cytotoxicity assay against P388 murine leukemia obviously disclosed that cytotoxicities of the synthesized compounds are comparable and almost half of that of natural (+)-duocarmycin A.