2-[(E)-1,2-diphenylethenyl]-5-methoxy-1H-indole | 622863-58-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-[(E)-1,2-diphenylethenyl]-5-methoxy-1H-indole
• 英文别名: (E)-2-(1,2-diphenylvinyl)-5-methoxy-1H-indole
• CAS: 622863-58-5
• 化学式: C₂₃H₁₉NO
• 分子量: 325.41
• InChiKey: WHBGLDOXZHARRY-KGENOOAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[(E)-1,2-diphenylethenyl]-5-methoxy-1H-indole 在 manganese(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 19.0h， 生成 9-methoxy-4,5-diphenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione
  参考文献：
  名称：

  4-Phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione Inhibitors of the Checkpoint Kinase Wee1. Structure−Activity Relationships for Chromophore Modification and Phenyl Ring Substitution

  摘要：

  High-throughput screening has identified a novel class of inhibitors of the checkpoint kinase Wee1, which have potential for use in cancer chemotherapy. These inhibitors are based on a 4-phenylpyrrolo[3,4-c]carbazole- 1,3(2H,6H)-dione template and have been shown by X-ray crystallography to bind at the ATP site of the enzyme. An extensive study of the effects of substitution around this template has been carried out, which has identified substituents which lead to improvements in potency and selectivity for Wee1. While retention of the maleimide ring and pendant 4-phenyl group is necessary for potency, replacement of the carbazole nitrogen by oxygen is well tolerated and results in improved Wee1 selectivity against the related checkpoint kinase Chk1. Wee1 potency and selectivity are also enhanced by the incorporation of lipophilic functionality at the 2'-position of the 4-phenyl ring, and Wee1 selectivity against Chk1 is favored by C3-C5 alkyl substitution of the carbazole nitrogen. These studies provide a basis for the design of active analogues of the pyrrolocarbazole lead with improved physical properties.

  DOI：

  10.1021/jm0512591
• 作为产物：
  描述：

  5-甲氧基-1H-吲哚-2-羧酸 在 manganese(IV) oxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 、 环己烷 为溶剂， 反应 1.67h， 生成 2-[(E)-1,2-diphenylethenyl]-5-methoxy-1H-indole
  参考文献：
  名称：

  4-Phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione Inhibitors of the Checkpoint Kinase Wee1. Structure−Activity Relationships for Chromophore Modification and Phenyl Ring Substitution

  摘要：

  High-throughput screening has identified a novel class of inhibitors of the checkpoint kinase Wee1, which have potential for use in cancer chemotherapy. These inhibitors are based on a 4-phenylpyrrolo[3,4-c]carbazole- 1,3(2H,6H)-dione template and have been shown by X-ray crystallography to bind at the ATP site of the enzyme. An extensive study of the effects of substitution around this template has been carried out, which has identified substituents which lead to improvements in potency and selectivity for Wee1. While retention of the maleimide ring and pendant 4-phenyl group is necessary for potency, replacement of the carbazole nitrogen by oxygen is well tolerated and results in improved Wee1 selectivity against the related checkpoint kinase Chk1. Wee1 potency and selectivity are also enhanced by the incorporation of lipophilic functionality at the 2'-position of the 4-phenyl ring, and Wee1 selectivity against Chk1 is favored by C3-C5 alkyl substitution of the carbazole nitrogen. These studies provide a basis for the design of active analogues of the pyrrolocarbazole lead with improved physical properties.

  DOI：

  10.1021/jm0512591

文献信息

• Iridium-Catalyzed Tandem Dehydrogenation/Hydroarylation Approach to Synthetically Versatile C2-Alkenyl N–H Indoles
  作者：Carlos Lázaro-Milla、José L. Mascareñas、Fernando López

  DOI：10.1021/acscatal.3c05841

  日期：2024.3.1

  Readily available N-carbamoyl indolines can be converted into highly valuable 2-alkenyl and 2-alkyl indoles in a one-pot reaction, through an autotandem catalytic cascade promoted by an iridium complex. The process entails a dehydrogenation reaction initiated by an iridium-promoted C(sp3)–H activation, the addition of the resulting indole to an alkyne -or alkene-partner, and a spontaneous loss of the carbamoyl

  通过铱络合物促进的自动串联催化级联，可以在一锅反应中将容易获得的N-氨基甲酰二氢吲哚转化为高价值的 2-烯基和 2-烷基吲哚。该过程需要由铱促进的 C(sp 3 )–H 活化引发的脱氢反应，将所得吲哚添加到炔烃或烯烃伴侣上，以及氨基甲酰基导向基团的自发损失。有趣的是，所得的C2-烯基吲哚可以参与由C-H活化引发的各种金属催化环化，包括正式的[4 + 1]和[4 + 2]环加成，以及交叉脱氢环化，从而使获得功能丰富的含氮杂环集合的不同途径。
• Ruthenium(II)-Catalyzed Direct Addition of Indole/Pyrrole C2–H Bonds to Alkynes
  作者：Libo Liang、Shaomin Fu、Dongen Lin、Xiao-Qi Zhang、Yuanfu Deng、Huanfeng Jiang、Wei Zeng

  DOI：10.1021/jo501460h

  日期：2014.10.17

  A ruthenium-catalyzed C2-hydroindolation of alkynes has been achieved. This protocol provides a rapid and concise access to kinds of 2-alkenyl-substituted N-(2-pyridyl)-indoles in which the pyridyl moiety can be easily removed to afford free (N H) indoles under mild conditions. Various arenes and alkynes, including electron-deficient and electronrich internal alkynes and terminal alkynes, allow for this transformation.
• US7094798B1
  申请人：——

  公开号：US7094798B1

  公开（公告）日：2006-08-22