methyl (1S)-5-benzyloxy-3-t-butoxycarbonyl-1-hydroxymethyl-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate | 157904-27-3

• 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: methyl (1S)-5-benzyloxy-3-t-butoxycarbonyl-1-hydroxymethyl-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate
• 英文别名: 6-O-tert-butyl 1-O-methyl (8S)-8-(hydroxymethyl)-4-phenylmethoxy-2-(trifluoromethyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylate
• CAS: 157904-27-3
• 化学式: C₂₆H₂₇F₃N₂O₆
• 分子量: 520.505
• InChiKey: LRXKDVSNCIVIEK-HNNXBMFYSA-N

物化性质

• 沸点：
  647.9±55.0 °C(predicted)
• 密度：
  1.355±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (1S)-5-benzyloxy-3-t-butoxycarbonyl-1-hydroxymethyl-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate 在 palladium on activated charcoal 盐酸 、 四氯化碳 、 甲酸铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成 methyl (8S)-8-(chloromethyl)-4-hydroxy-2-(trifluoromethyl)-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate
  参考文献：
  名称：

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

  摘要：

  The title synthesis was achieved by employing oxidative cyclization of the enaminoester as a key step. Some of these novel 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) derivatives, dl-10c,d, (+)-10d, and (S)-21b were found to exhibit antitumor activity against murine leukemia and murine solid tumors more prominent than that of the known CPI derivatives dl-4 and the clinical trial candidates 5 and 7. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00288-6
• 作为产物：
  描述：

  4,4,4-三氟巴豆酸甲酯 在 palladium diacetate 、 2,4-滴二甲胺盐 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 11.5h， 生成 methyl (1S)-5-benzyloxy-3-t-butoxycarbonyl-1-hydroxymethyl-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate
  参考文献：
  名称：

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

  摘要：

  The title synthesis was achieved by employing oxidative cyclization of the enaminoester as a key step. Some of these novel 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) derivatives, dl-10c,d, (+)-10d, and (S)-21b were found to exhibit antitumor activity against murine leukemia and murine solid tumors more prominent than that of the known CPI derivatives dl-4 and the clinical trial candidates 5 and 7. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00288-6

文献信息

• Trifluoromethylpyrroloindolecarboxylic acid ester and process for
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：US05629430A1

  公开（公告）日：1997-05-13

  Trifluoromethylpyrroloindolecarboxylic acid ester derivatives, and optical isomers and pharmaceutically acceptable salts thereof are provided which are represented by the general formula (1): ##STR1## or the general formula (2): ##STR2## The compounds are antineoplastic agents which are selective to cancer cells, effective also to solid cancer, and less toxic.

  提供了三氟甲基吡咯吲哌酮酸酯衍生物，以及它们的光学异构体和药学上可接受的盐，其通式表示为（1）： ##STR1## 或通式（2）： ##STR2## 这些化合物是选择性作用于癌细胞的抗肿瘤剂，对实体癌也有效，并且毒性较小。