methyl (1S)-1-acetoxymethyl-5-benzyloxy-3-t-butoxycarbonyl-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate | 157904-26-2

• 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)-1-acetoxymethyl-5-benzyloxy-3-t-butoxycarbonyl-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-(acetyloxymethyl)-4-phenylmethoxy-2-(trifluoromethyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylate
• CAS: 157904-26-2
• 化学式: C₂₈H₂₉F₃N₂O₇
• 分子量: 562.543
• InChiKey: QMCITQTYXOYEKJ-KRWDZBQOSA-N

物化性质

• 沸点：
  649.3±55.0 °C(predicted)
• 密度：
  1.330±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl (1S)-1-acetoxymethyl-5-benzyloxy-3-t-butoxycarbonyl-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate 在 palladium on activated charcoal 盐酸 、 四氯化碳 、 氢溴酸 、 甲酸铵 、 potassium carbonate 、 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 、 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 14.5h， 生成 (S)-8-Bromomethyl-4-hydroxy-2-trifluoromethyl-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-1-carboxylic acid methyl ester
  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：

  tert-butyl (3S)-3-(acetyloxymethyl)-6-phenylmethoxy-5-[(1,1,1-trifluoro-4-methoxy-4-oxobut-2-en-2-yl)amino]-2,3-dihydroindole-1-carboxylate 在 palladium diacetate 、 2,4-滴二甲胺盐 作用下， 反应 3.5h， 以58%的产率得到methyl (1S)-1-acetoxymethyl-5-benzyloxy-3-t-butoxycarbonyl-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。