1-phenyl-2-methoxyindole-3-carboxaldehyde | 68096-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-phenyl-2-methoxyindole-3-carboxaldehyde
• 英文别名: 2-methoxy-1-phenylindole-3-carboxaldehyde；2-Methoxy-1-phenyl-indol-3-carbaldehyd；2-methoxy-1-phenyl-indole-3-carbaldehyde；2-Methoxy-1-phenylindole-3-carbaldehyde
• CAS: 68096-85-5
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: NXKIUWJMOHKBFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-吲哚酮 、 1-phenyl-2-methoxyindole-3-carboxaldehyde 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以40%的产率得到(3E)-3-[(2-methoxy-1-phenylindol-3-yl)methylidene]-1H-indol-2-one
  参考文献：
  名称：

  Substituted E-3-(3-indolylmethylene)1,3-dihydroindol-2-ones with antiproliferative activity. Study of the effects on HL-60 leukemia cells

  摘要：

  The synthesis of new substituted E-3-(3-indolylmethylene)1,3-dihydroindol-2-ones is reported. The antiproliferative activity was evaluated according to protocols available at the National Cancer Institute (NCI), Bethesda, MD. The action of the most active compound 10 was further investigated in HL-60 leukemia cells. Results obtained show that it causes a block in cell cycle progression, with cell arrest in the G2/M phase, associated with activation of apoptosis accompanied with increased oxidative stress and deregulation of the homeostasis of divalent cations, with significant increase in the cellular concentrations of free Ca2+ and Mg2+. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.004

文献信息

• Thienylvinylindoles as inhibitors of mitochondrial NADH dehydrogenase
  作者：Aldo Andreani、Mirella Rambaldi、Alessandra Locatelli、Alberto Leoni、Anna Ghelli、Mauro Degli Esposti

  DOI：10.1016/0031-6865(94)90025-6

  日期：1994.7

  were synthesized and tested as specific inhibitors of mitochondrial NADH dehydrogenase. The position of the phenyl ring and the geometrical configuration play an important role in the activity and specificity of these derivatives. In order to study the mechanism of action of these thienylvinylindoles, their activity was compared with that of known inhibitors in a new test employing exogenous quinones

  结合先前的研究，合成了带有2-或3-噻吩基的新苯基吲哚并作为线粒体NADH脱氢酶的特异性抑制剂进行了测试。苯环的位置和几何构型在这些衍生物的活性和特异性中起重要作用。为了研究这些噻吩乙烯基吲哚的作用机理，在使用外源醌的新试验中将它们的活性与已知抑制剂的活性进行了比较。
• 3-(2-Thienylvinyl)indoles as potential specific inhibitors of the energy metabolism in helminthic parasites
  作者：A Andreani、M Rambaldi、A Locatelli、F Andreani、G Poglayen、M Degli Esposti

  DOI：10.1016/0223-5234(92)90094-h

  日期：1992.10

  Seven indoles bearing a thienylvinyl group, present in the well known anthelmintic drug pyrantel, were synthesized and tested as inhibitors of the mitochondrial energy metabolism in order to recognize selective compounds (active on the mitochondria of helminthic parasites but inactive on the mitochondria of birds and mammals). 1-Phenyl-2-chloro-3-(2-thienylvinyl)indole 14, showing this biochemical behaviour, was also tested on Parascaris equorum living worms, confirming its activity on the energy metabolism.
• Substituted E-3-(3-indolylmethylene)1,3-dihydroindol-2-ones with antiproliferative activity. Study of the effects on HL-60 leukemia cells
  作者：Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Concettina Cappadone、Giovanna Farruggia、Stefano Iotti、Lucia Merolle、Maddalena Zini、Claudio Stefanelli

  DOI：10.1016/j.ejmech.2014.04.004

  日期：2014.5

  The synthesis of new substituted E-3-(3-indolylmethylene)1,3-dihydroindol-2-ones is reported. The antiproliferative activity was evaluated according to protocols available at the National Cancer Institute (NCI), Bethesda, MD. The action of the most active compound 10 was further investigated in HL-60 leukemia cells. Results obtained show that it causes a block in cell cycle progression, with cell arrest in the G2/M phase, associated with activation of apoptosis accompanied with increased oxidative stress and deregulation of the homeostasis of divalent cations, with significant increase in the cellular concentrations of free Ca2+ and Mg2+. (C) 2014 Elsevier Masson SAS. All rights reserved.