2-[(E)-2-(3,4-dimethoxyphenyl)-1-ethenyl]-3,3-dimethyl-3H-indole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(E)-2-(3,4-dimethoxyphenyl)-1-ethenyl]-3,3-dimethyl-3H-indole
• 英文别名: (E)-2-(3,4-dimethoxystyryl)-3,3-dimethyl-3H-indole；Azj-32-B；2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-3,3-dimethylindole
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: HFUQEVGAUVOLDS-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(E)-2-(3,4-dimethoxyphenyl)-1-ethenyl]-3,3-dimethyl-3H-indole 在 碘 、 silver perchlorate 作用下， 以 乙腈 为溶剂， 生成 2,3-dimethoxy-7,7-dimethyl-7H-indolo[1,2-a]quinolinylium perchlorate
  参考文献：
  名称：

  涉及CN键形成的吲哚基苯基乙烯的光化学电环化。

  摘要：

  [反应：见正文]描述了一种新型的吲哚基苯基乙烯向多环杂芳族阳离子的氧化光脱氢环化，收率很高。从反导衍生物开始，光转化是一个多步骤过程。该方法包括两个光化学反应和反式-顺式异构化反应，然后是涉及形成CN键的1-氮杂-1,3,5-己三烯环电反应。环化产物通过与空气或碘中的氧消除氢化物而获得稳定的杂芳族阳离子。

  DOI：

  10.1021/ol034848e
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 、 3,4-二甲氧基苯甲醛 在 盐酸 作用下， 以 水 、 乙醇 为溶剂， 反应 4.5h， 以51.5%的产率得到2-[(E)-2-(3,4-dimethoxyphenyl)-1-ethenyl]-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.
• Photochemical Electrocyclization of the Indolinylphenylethenes Involving a C−N Bond Formation
  作者：Olga A. Fedorova、Yuri V. Fedorov、Elena N. Andryukhina、Sergey P. Gromov、Michael V. Alfimov、René Lapouyade

  DOI：10.1021/ol034848e

  日期：2003.11.1

  [reaction: see text] A novel oxidative photodehydrocyclization of indolinylphenylethenes to a polycyclic heteroaromatic cation with good yields was described. Starting from the trans derivative, the phototransformation is a multistep process. The process includes two photochemical reactions and a trans-cis isomerization reaction, followed by an 1-aza-1,3,5-hexatrienic electrocyclic reaction involving

  [反应：见正文]描述了一种新型的吲哚基苯基乙烯向多环杂芳族阳离子的氧化光脱氢环化，收率很高。从反导衍生物开始，光转化是一个多步骤过程。该方法包括两个光化学反应和反式-顺式异构化反应，然后是涉及形成CN键的1-氮杂-1,3,5-己三烯环电反应。环化产物通过与空气或碘中的氧消除氢化物而获得稳定的杂芳族阳离子。