2,3-dihydro-5,6-dimethoxy-1-methyl-2-oxo-1H-indole | 74054-33-4

• 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: 2,3-dihydro-5,6-dimethoxy-1-methyl-2-oxo-1H-indole
• 英文别名: 5,6-dimethoxy-1-methyl-indolin-2-one；5,6-Dimethoxy-1-methyl-indolin-2-on；5,6-dimethoxy-1-methyl-3H-indol-2-one
• CAS: 74054-33-4
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: HFMYKOSYSGHBQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-5,6-dimethoxy-1-methyl-2-oxo-1H-indole 、 (4-formylphenyl)-3-phenylurea 在 哌啶 作用下， 以 乙醇 为溶剂， 以32%的产率得到C₂₅H₂₃N₃O₄
  参考文献：
  名称：

  Synthesis and RET protein kinase inhibitory activity of 3-arylureidobenzylidene-indolin-2-ones

  摘要：

  A novel series of 3-arylureidobenzylidene-indolin-2-ones was synthesized and their inhibitory activity against Ret tyrosine kinase investigated in comparison with the Ret inhibitor RPI-1 as a reference compound for this series. A few compounds were able to revert the RETC634R oncogene-transformed morphologic phenotype of NIH3T3(MEN2A) cells and showed a selective antiproliferative activity against these cells as compared to parental NIH3T3 cells or NIH3T3 cells transformed with a non-tyrosine kinase oncogene (NIH3T3(H-RAS)). Inhibition of Ret enzyme activity by effective derivatives was confirmed in a kinase assay. Structure-activity relationship indicated a favourable activity for 5,6-dimethoxyindolinone derivatives with H, OH, or OMe in the para position of the distal aryl ring. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.091
• 作为产物：
  描述：

  N-methyl-2-bromo-4,5-dimethoxyphenylacetamide 在 sodium hydride 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 以63.4%的产率得到2,3-dihydro-5,6-dimethoxy-1-methyl-2-oxo-1H-indole
  参考文献：
  名称：

  杂环化合物合成的研究。第865部分：通过分子内亲核芳族取代的新颖合成吲哚衍生物

  摘要：

  环化ñ - （2-溴-4,5-二甲氧基苯乙基）乙酰胺（6），得到1-乙酰基-2,3-二氢-5,6-二甲氧基-1- ħ -吲哚使用（13）通过分子内的亲核芳族取代钠二甲基甲酰胺中的氢化物和卤化亚铜。还以类似方式由相应的酰胺（8）和（10）以及氨基甲酸酯（12）合成二氢吲哚（14），（15）和（16）。通过氧化和随后的碱水解，将二氢吲哚（13），（14）和（16）以优异的产率转化为吲哚（20）和（21）。还可以在相似的反应条件下由苯基乙酰胺（24）和（25）制备2-氧吲哚（26）和（27）。

  DOI：

  10.1039/p19810000290

文献信息

• Kametani, Tetsuji; Ohsawa, Tatsushi; Ihara, Masataka, Heterocycles, 1980, vol. 14, # 3, p. 277 - 280
  作者：Kametani, Tetsuji、Ohsawa, Tatsushi、Ihara, Masataka

  DOI：——

  日期：——
• 68. The oxidation of β-3 : 4-dihydroxyphenylethylmethylamine with silver oxide. The isolation of 5 : 6-dihydroxy-1-methylindole and a synthesis of 5 : 6-dimethoxy-1-methylindole
  作者：Harold Burton

  DOI：10.1039/jr9320000546

  日期：——
• KAMETANI TETSUJI; OHSAWA TATSUSHI; IHARA MASATAKA, J. CHEM. SOC. PERKIN TRANS., 1981, PART 1, NO 1, 290-294
  作者：KAMETANI TETSUJI、 OHSAWA TATSUSHI、 IHARA MASATAKA

  DOI：——

  日期：——
• Synthesis and RET protein kinase inhibitory activity of 3-arylureidobenzylidene-indolin-2-ones
  作者：Eleonora Rizzi、Giuliana Cassinelli、Sabrina Dallavalle、Cinzia Lanzi、Raffaella Cincinelli、Raffaella Nannei、Giuditta Cuccuru、Franco Zunino

  DOI：10.1016/j.bmcl.2007.04.091

  日期：2007.7

  A novel series of 3-arylureidobenzylidene-indolin-2-ones was synthesized and their inhibitory activity against Ret tyrosine kinase investigated in comparison with the Ret inhibitor RPI-1 as a reference compound for this series. A few compounds were able to revert the RETC634R oncogene-transformed morphologic phenotype of NIH3T3(MEN2A) cells and showed a selective antiproliferative activity against these cells as compared to parental NIH3T3 cells or NIH3T3 cells transformed with a non-tyrosine kinase oncogene (NIH3T3(H-RAS)). Inhibition of Ret enzyme activity by effective derivatives was confirmed in a kinase assay. Structure-activity relationship indicated a favourable activity for 5,6-dimethoxyindolinone derivatives with H, OH, or OMe in the para position of the distal aryl ring. (C) 2007 Elsevier Ltd. All rights reserved.
• Studies on the syntheses of heterocyclic compounds. Part 865. A novel synthesis of indole derivatives by intramolecular nucleophilic aromatic substitution
  作者：Tetsuji Kametani、Tatsushi Ohsawa、Masataka Ihara

  DOI：10.1039/p19810000290

  日期：——

  Cyclisation of N-(2-bromo-4,5-dimethoxyphenethyl)acetamide (6) afforded 1-acetyl-2,3-dihydro-5,6-dimethoxy-1H-indole (13) by intramolecular nucleophilic aromatic substitution using sodium hydride and cuprous halide in dimethylformamide. The dihydroindoles (14), (15), and (16) were also synthesised from the corresponding amides (8) and (10) and the carbamate (12) in a similar manner. The dihydroindoles

  环化ñ - （2-溴-4,5-二甲氧基苯乙基）乙酰胺（6），得到1-乙酰基-2,3-二氢-5,6-二甲氧基-1- ħ -吲哚使用（13）通过分子内的亲核芳族取代钠二甲基甲酰胺中的氢化物和卤化亚铜。还以类似方式由相应的酰胺（8）和（10）以及氨基甲酸酯（12）合成二氢吲哚（14），（15）和（16）。通过氧化和随后的碱水解，将二氢吲哚（13），（14）和（16）以优异的产率转化为吲哚（20）和（21）。还可以在相似的反应条件下由苯基乙酰胺（24）和（25）制备2-氧吲哚（26）和（27）。