3-<2-(p-Methoxyphenyl)-vinyl>indol | 53645-35-5

• 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: 3-<2-(p-Methoxyphenyl)-vinyl>indol
• 英文别名: 3-(4-methoxy-styryl)-indole；3-[2-(4-methoxyphenyl)ethenyl]-1H-indole
• CAS: 53645-35-5
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: KTHIFOAZIPPOMY-UHFFFAOYSA-N

物化性质

• 熔点：
  198-199 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  457.5±14.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  3-<2-(p-Methoxyphenyl)-vinyl>indol 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以65%的产率得到3-(3-indolyl)-2-(4-methoxyphenyl)-1-(4-methoxybenzyl)-1,2,3,4-tetrahydro cyclopent[b]indole
  参考文献：
  名称：

  Exploring stereoselectivity of 3-indolyl cyclopent[b]indoles: A parallel synthesis and anti-EGFR study on human cancer cells

  摘要：

  We synthesized a series of novel 3-indolyl cyclopent[b]indoles by trifluoroacetic acid mediated cyclodimerizations. The reaction showed high stereoselectivity and moderate to good yields. The influencing factors for stereoselectivity were systematically analyzed and a stepwise reaction mechanism was proposed. The cell viability tests in two colon and two lung cancer cell lines indicated the 1-benzyl-2phenyl-group in 3-indolyl cyclopent[b]indoles was critical for the observed lower IC(50)s in these compounds. Western blot analysis demonstrated that the compound inhibited the expression and phosphorylation of EGFR through altered HSP90 expression. Further cell cycle and cell cycle check point protein analyses showed expected anti-cellular proliferation and cell cycle arresting properties associated with suppressed EGFR expression and phosphorylation. These data revealed a novel molecular mechanism explaining the observed cytotoxicities for these compounds. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.012

文献信息

• Catalyst-free and atom-economic synthesis of substituted 1-acetyl and 1-hydroxyl carbazoles
  作者：Feng Yu、Dan Li、Yu Wei、Rui-Ming Kang、Qi-Xiang Guo

  DOI：10.1016/j.tet.2018.02.066

  日期：2018.4

  The first-ever Diels-Alder reactions of 3-alkenyl indoles with a conjugated alkynyl ketone are reported. These reactions proceed in an atom-economic manner without a catalyst and give various substituted 1-acetyl carbazoles in moderate to excellent yields. These products can be converted to 1-hydroxyl carbazoles in high yields under mild reaction conditions.

  报道了3-烯基吲哚与共轭炔基酮的首次Diels-Alder反应。这些反应在没有催化剂的情况下以原子经济的方式进行，并以中等至优异的产率得到各种取代的1-乙酰基咔唑。这些产物可以在温和的反应条件下高产率地转化为1-羟基咔唑。
• Exploring stereoselectivity of 3-indolyl cyclopent[b]indoles: A parallel synthesis and anti-EGFR study on human cancer cells
  作者：Dacheng Fan、Weizhi Sun、Peiju Qiu、Zhiyong Wu、Yantuan Li、Shengbiao Wan、Tao Jiang、Lijuan Zhang

  DOI：10.1016/j.ejmech.2013.08.012

  日期：2014.3

  We synthesized a series of novel 3-indolyl cyclopent[b]indoles by trifluoroacetic acid mediated cyclodimerizations. The reaction showed high stereoselectivity and moderate to good yields. The influencing factors for stereoselectivity were systematically analyzed and a stepwise reaction mechanism was proposed. The cell viability tests in two colon and two lung cancer cell lines indicated the 1-benzyl-2phenyl-group in 3-indolyl cyclopent[b]indoles was critical for the observed lower IC(50)s in these compounds. Western blot analysis demonstrated that the compound inhibited the expression and phosphorylation of EGFR through altered HSP90 expression. Further cell cycle and cell cycle check point protein analyses showed expected anti-cellular proliferation and cell cycle arresting properties associated with suppressed EGFR expression and phosphorylation. These data revealed a novel molecular mechanism explaining the observed cytotoxicities for these compounds. (C) 2014 Elsevier Masson SAS. All rights reserved.