Methyl 1-chloromethyl-5-hydroxy-3-(5-methoxy-1H-indol-2-ylcarbonyl)-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate | 194093-68-0

• 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: Methyl 1-chloromethyl-5-hydroxy-3-(5-methoxy-1H-indol-2-ylcarbonyl)-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate
• 英文别名: methyl 8-(chloromethyl)-4-hydroxy-6-(5-methoxy-1H-indole-2-carbonyl)-2-(trifluoromethyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1-carboxylate
• CAS: 194093-68-0
• 化学式: C₂₄H₁₉ClF₃N₃O₅
• 分子量: 521.88
• InChiKey: BZDNZFQNKQUEDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 1-chloromethyl-5-hydroxy-3-(5-methoxy-1H-indol-2-ylcarbonyl)-7-trifluoromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-8-carboxylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以82%的产率得到methyl 10-(5-methoxy-1H-indole-2-carbonyl)-7-oxo-4-(trifluoromethyl)-5,10-diazatetracyclo[7.4.0.01,12.02,6]trideca-2(6),3,8-triene-3-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：

  3-acetoxymethyl-5-amino-6-benzyloxy-1-t-butoxycarbonyl-2,3-dihydro-1H-indole 在 palladium on activated charcoal 盐酸 、 四氯化碳 、 palladium diacetate 、 甲酸铵 、 2,4-滴二甲胺盐 、 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 17.5h， 生成 Methyl 1-chloromethyl-5-hydroxy-3-(5-methoxy-1H-indol-2-ylcarbonyl)-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.

  提供由一般式（1）或一般式（2）表示的三氟甲基吡咯吲啉羧酸酯衍生物、其光学异构体和药学上可接受的盐：##STR1## ##STR2## 这些化合物是选择性作用于癌细胞的抗肿瘤剂，对实体肿瘤也有效，并且毒性较低。
• TRIFLUOROMETHYLPYRROLOINDOLE CARBOXYLIC ESTER DERIVATIVE AND PROCESS FOR PRODUCING THE SAME
  申请人：KYORIN PHARMACEUTICAL CO., LTD.

  公开号：EP0656360A1

  公开（公告）日：1995-06-07

  Trifluoromethylpyrroloindole carboxylic ester derivatives represented by general formulae (1) and (2) having an antitumor activity, optically active isomers thereof, and pharmacologically acceptable salts thereof, wherein R represents lower alkyl; R¹ represents an α-amino acid residue, etc.; R² represents hydrogen, a hydroxyl-protecting group, etc.; and Y represents halogen, arylsulfonyloxy, etc.

  通式(1)和(2)代表的具有抗肿瘤活性的三氟甲基吡咯吲哚羧酸酯衍生物、其光学活性异构体及其药理上可接受的盐，其中R代表低级烷基；R¹代表α-氨基酸残基等；R²代表氢、羟基保护基等；Y代表卤素、芳基磺酰氧基等。
• US5629430A
  申请人：——

  公开号：US5629430A

  公开（公告）日：1997-05-13