1-[(4-甲基苯基)甲基]-1H-吲哚-3-甲醇 | 664317-83-3

• 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
• 中文名称: 1-[(4-甲基苯基)甲基]-1H-吲哚-3-甲醇
• 英文名称: 1-[(4-methylphenyl)methyl]-1H-indole-3-methanol
• 英文别名: [1-(4-methylbenzyl)-1H-indol-3-yl]methanol；[1-[(4-methylphenyl)methyl]indol-3-yl]methanol
• CAS: 664317-83-3
• 化学式: C₁₇H₁₇NO
• mdl: MFCD04089279
• 分子量: 251.328
• InChiKey: ZRWCGJOQBCKMTO-UHFFFAOYSA-N

物化性质

• 沸点：
  466.5±33.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-[(4-甲基苯基)甲基]-1H-吲哚-3-甲醛 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 1-[(4-甲基苯基)甲基]-1H-吲哚-3-甲醇
  参考文献：
  名称：

  Analogues and Derivatives of Oncrasin-1, a Novel Inhibitor of the C-Terminal Domain of RNA Polymerase II and Their Antitumor Activities

  摘要：

  To optimize the antitumor activity of oncrasin-1, a small molecule RNA polymerase II inhibitor, We evaluated 69 oncrasin-1 analogues for their cytotoxic activity against normal human epithelial cells and K-Ras mutant tumor cells. About 40 of those compounds were as potent as or more potent than oncrasin-1 in tumor cells and had a minimal cytotoxic effect on normal cells. Structure activity relationship analysis revealed that most of the active compounds contained either a hydroxymethyl group or an aldehyde group as a substitute at the 3-position of the indole. Both electron-donating and electron-withdrawing groups in the benzene ring were well tolerated. The hydroxymethyl compounds ranged from equipotent with to 100 times as potent as the corresponding aldehyde compounds. We tested three active analogues' effect on RNA, polymerase phosphorylation and found that they all inhibited phosphorylation of the C-terminal domain of RNA polymerase suggesting that the active compounds might act through the same mechanisms as oncrasin-1.

  DOI：

  10.1021/jm101417n

文献信息

• Indole-3-carbinol (I3C) derivatives and methods
  申请人：The Regents of the University of California

  公开号：US20030087946A1

  公开（公告）日：2003-05-08

  The invention provides methods and compositions relating to novel bioactive derivatives of indole-3-carbinol (I3C), including pharmaceuticals comprising a pharmaceutically acceptable excipient and a compound of the general formula: 1 which inhibits tumor cell growth. Methods of inhibiting targeted cell growth include contacting a target cell with a disclosed compound under conditions whereby the growth the target cell is inhibited, and methods for evaluating the growth inhibitory activity of the compounds include contacting a cell with an effective amount of the compound and measuring the CDK6 expression in the cell, wherein a reduction in CDK6 expression correlates with the growth inhibitory activity of the compound.

  本发明提供了与吲哚-3-甲醇（I3C）的新型生物活性衍生物有关的方法和组合物，包括由药学上可接受的赋形剂和通式化合物组成的药物： 1 该化合物可抑制肿瘤细胞生长。抑制靶细胞生长的方法包括在抑制靶细胞生长的条件下使靶细胞与所公开的化合物接触，评估化合物生长抑制活性的方法包括使细胞与有效量的化合物接触并测量细胞中 CDK6 的表达，其中 CDK6 表达的降低与化合物的生长抑制活性相关。
• US6150395A
  申请人：——

  公开号：US6150395A

  公开（公告）日：2000-11-21
• US6369095B1
  申请人：——

  公开号：US6369095B1

  公开（公告）日：2002-04-09
• US6656963B2
  申请人：——

  公开号：US6656963B2

  公开（公告）日：2003-12-02
• [EN] INDOLE-3-CARBINOL (I3C) DERIVATIVES<br/>[FR] DERIVES D'INDOLE-3-CARBINOL (I3C)
  申请人：UNIV CALIFORNIA

  公开号：WO2001030344A1

  公开（公告）日：2001-05-03

  The invention provides methods and compositions relating to novel bioactive derivatives of indole-3-carbinol (I3C), including pharmaceuticals comprising a pharmaceutically acceptable excipient and a compound of general formula (I) which inhibits tumor cell growth. Methods of inhibiting targeted cell growth include contacting a target cell with a disclosed compound under conditions whereby the growth the target cell is inhibited, and methods for evaluating the growth inhibitory activity of the compounds include contacting a cell with an effective amount of the compound and measuring the CDK6 expression in the cell, wherein a reduction in CDK6 expression correlates with the growth inhibitory activity of the compound.