4-(4-hydroxyphenyl)-6,7-dimethoxy-2H-pyrido[3,4-b]indol-1(9H)-one | 1048685-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(4-hydroxyphenyl)-6,7-dimethoxy-2H-pyrido[3,4-b]indol-1(9H)-one
• 英文别名: 4-(4-hydroxyphenyl)-6,7-dimethoxy-2,9-dihydropyrido[3,4-b]indol-1-one
• CAS: 1048685-43-3
• 化学式: C₁₉H₁₆N₂O₄
• 分子量: 336.347
• InChiKey: MKOGRTXXHLJYQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-[2-(4-hydroxyphenyl)-2-oxoethyl]-5,6-dimethoxy-1H-indole-2-carboxamide 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 生成 4-(4-hydroxyphenyl)-6,7-dimethoxy-2H-pyrido[3,4-b]indol-1(9H)-one
  参考文献：
  名称：

  Synthesis, Modeling, and RET Protein Kinase Inhibitory Activity of 3- and 4-Substituted β-Carbolin-1-ones

  摘要：

  A series of beta-carbolin-2-ones and 3,10-dihydro-2H-azepino[3,4-b]indol-1-ones have been designed, synthesized, and evaluated as RET protein kinase inhibitors oil the basis Of their Structural similarity with the prototype indolin-2-one RPI-1. Some beta-carbolin-2-ones (structure 2) showed ail ability to inhibit RET enzymatic activity in vitro and proliferation of RETC634R oncogene-transformed NIH3T3 cells comparable to that of the reference compound. The docking analysis of the interaction of these compounds with the crystallographic structure of RET tyrosine kinase domain suggested a new binding interaction scheme different from the one proposed during their design. The rigid structure of the compounds of this series represents a new scaffold with potential advantages in the design of RET protein kinase inhibitors.

  DOI：

  10.1021/jm8007823

文献信息

• Intramolecular Friedel-Crafts Reaction of Indoles with Carbonyl Groups: A Simple Synthesis of 3- and 4-Substituted β-Carbolin-1-ones
  作者：Sabrina Dallavalle、Raffaella Cincinelli、Lucio Merlini

  DOI：10.1055/s-2008-1072613

  日期：2008.5

  The intramolecular Friedel-Crafts reaction of indole-2-carboxylic acid β-oxoamides catalyzed by trifluoroacetic acid or InCl 3 , is a convenient method for the synthesis of 3-aryl-, 4-aryl-, and 4-alkyl-β-carbolin-1-ones.

  三氟乙酸或InCl 3 催化吲哚-2-羧酸β-氧代酰胺的分子内Friedel-Crafts反应是合成3-芳基-、4-芳基-和4-烷基-β-咔啉的便捷方法-1个。