(E)-2-(3-methylstyryl)-3,3-dimethyl-3H-indole | 1448422-53-4

• 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: (E)-2-(3-methylstyryl)-3,3-dimethyl-3H-indole
• 英文别名: Azj-22-B；3,3-dimethyl-2-[(E)-2-(3-methylphenyl)ethenyl]indole
• CAS: 1448422-53-4
• 化学式: C₁₉H₁₉N
• 分子量: 261.367
• InChiKey: MTNNOTDQHUNHQS-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 、 3-甲基苯甲醛 在 盐酸 作用下， 以 水 、 乙醇 为溶剂， 反应 4.5h， 以52.6%的产率得到(E)-2-(3-methylstyryl)-3,3-dimethyl-3H-indole
  参考文献：
  名称：

  Elaboration of thorough simplified vinca alkaloids as antimitotic agents based on pharmacophore similarity

  摘要：

  Thorough simplification of vinca alkaloids based on pharmacophore similarity has been conducted. A concise process for the syntheses of target compounds was successfully developed with yields from poor to excellent (19-98%). Cell growth inhibitory activities of these synthesized compounds were evaluated in five cancer cell lines including MCF-7, MDA-MB-231, HepG2, HepG2/ADM and K562. Almost all compounds exhibited moderate antitumor activity with optimal IC50 value of 0.89 +/- 0.07 mu M in MCF-7 cells. Investigation of structure-activity relationship (SAR) indicates that electron-withdraw substituents on the ring contribute to the enhancement of the antitumor activities. The simplified vinca alkaloids are confirmed as antimitotic agents, which inhibit the polymerization of tubulin just like vinblastine. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.057

文献信息

• Elaboration of thorough simplified vinca alkaloids as antimitotic agents based on pharmacophore similarity
  作者：Jing Zheng、Lijuan Deng、Minfeng Chen、Xuzhi Xiao、Shengwei Xiao、Cuiping Guo、Gaokeng Xiao、Liangliang Bai、Wencai Ye、Dongmei Zhang、Heru Chen

  DOI：10.1016/j.ejmech.2013.04.057

  日期：2013.7

  Thorough simplification of vinca alkaloids based on pharmacophore similarity has been conducted. A concise process for the syntheses of target compounds was successfully developed with yields from poor to excellent (19-98%). Cell growth inhibitory activities of these synthesized compounds were evaluated in five cancer cell lines including MCF-7, MDA-MB-231, HepG2, HepG2/ADM and K562. Almost all compounds exhibited moderate antitumor activity with optimal IC50 value of 0.89 +/- 0.07 mu M in MCF-7 cells. Investigation of structure-activity relationship (SAR) indicates that electron-withdraw substituents on the ring contribute to the enhancement of the antitumor activities. The simplified vinca alkaloids are confirmed as antimitotic agents, which inhibit the polymerization of tubulin just like vinblastine. (C) 2013 Elsevier Masson SAS. All rights reserved.