4-Benzyloxy-8-chloromethyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,2,6-tricarboxylic acid 6-tert-butyl ester 1,2-dimethyl ester | 156905-83-8

• 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: 4-Benzyloxy-8-chloromethyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,2,6-tricarboxylic acid 6-tert-butyl ester 1,2-dimethyl ester
• CAS: 156905-83-8
• 化学式: C₂₇H₂₉ClN₂O₇
• 分子量: 528.989
• InChiKey: KNEVNUPPGDYAGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  107.16
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-Benzyloxy-8-chloromethyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,2,6-tricarboxylic acid 6-tert-butyl ester 1,2-dimethyl ester 在 palladium on activated charcoal 盐酸 、 甲酸铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 dimethyl 8-(chloromethyl)-4-hydroxy-6-[5-(1H-indole-2-carbonylamino)-1H-indole-2-carbonyl]-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis and antitumor activity of novel cyclopropapyrroloindole (CPI) derivatives bearing bis(methoxycarbonyl) groups

  摘要：

  The title synthesis was achieved by employing oxidative cyclization of the enaminodiester prepared by Michael addition of the 5-aminoindoline with dimethyl acetylenedicarboxylate, as a key step. Some of these novel bis(methoxycarbonyl)cyclopropapyrroloindole (MC(2)CPI) derivatives 9c, d and their seco-chlorides 18c, d were found to exhibit prominent cytotoxicity and antitumor activity against P388 murine leukemia. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00099-1
• 作为产物：
  描述：

  8-Acetoxymethyl-4-benzyloxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,2,6-tricarboxylic acid 6-tert-butyl ester 1,2-dimethyl ester 在 四氯化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 4-Benzyloxy-8-chloromethyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,2,6-tricarboxylic acid 6-tert-butyl ester 1,2-dimethyl ester
  参考文献：
  名称：

  Synthesis and antitumor activity of novel cyclopropapyrroloindole (CPI) derivatives bearing bis(methoxycarbonyl) groups

  摘要：

  The title synthesis was achieved by employing oxidative cyclization of the enaminodiester prepared by Michael addition of the 5-aminoindoline with dimethyl acetylenedicarboxylate, as a key step. Some of these novel bis(methoxycarbonyl)cyclopropapyrroloindole (MC(2)CPI) derivatives 9c, d and their seco-chlorides 18c, d were found to exhibit prominent cytotoxicity and antitumor activity against P388 murine leukemia. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00099-1