2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carbaldehyde | 108160-50-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carbaldehyde
• 英文别名: 2-(2-oxobenzopyran-3-yl)indole-3-carboxaldehyde；2-(2-oxochromen-3-yl)-1H-indole-3-carbaldehyde
• CAS: 108160-50-5
• 化学式: C₁₈H₁₁NO₃
• 分子量: 289.29
• InChiKey: MHLDQAJEDUTSMC-UHFFFAOYSA-N

物化性质

• 熔点：
  246-248 °C(Solv: 1,4-dioxane (123-91-1))
• 沸点：
  593.7±50.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.07
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carbaldehyde 在 吡啶 、 potassium permanganate 、 sodium hydroxide 作用下， 反应 5.0h， 以30%的产率得到2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carboxylic acid
  参考文献：
  名称：

  Some new indole–coumarin hybrids; Synthesis, anticancer and Bcl-2 docking studies

  摘要：

  Hybrid molecules have attracted attention for their improved biological activity, selectivity and lesser side effects profile, distinct from their individual components. In the quest for novel anticancer drug entities, three series of indole-coumarin hybrids - 3-(1-benzyl-1H-indol-2-yl)-2H-chromen-2-ones, 2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carbaldehydes and 2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carboxylic acids were synthesized. All the synthesized compounds were characterized by spectral techniques like IR, H-1 NMR, C-13 NMR, mass spectrometry and elemental analysis. In silico docking studies of synthesized molecules with apoptosis related gene Bcl-2 that is recognized to play an important role in tumerogenesis were carried out. Dose-dependent cytotoxic effect of the compounds in human breast adenocarcinoma (MCF-7) and normal cell lines were assessed using MTT assay and compared with that of the standard marketed drug, Vincristine. Compound 4c had a highly lipophilic bromine substituent capable of forming halogen bond and was identified as a potent molecule both in docking as well as cytotoxicity studies. Flow cytometric cell cycle analysis of 4c exhibited apoptotic mode of cell death due to cell cycle arrest in G2/M phase. Structure activity relationship of these hybrid molecules was also studied to determine the effect of steric and electronic properties of the substituents on cell viability. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.10.001
• 作为产物：
  描述：

  ω-anilino-3-acetylbenzopyran-2-one 在 苯胺氢溴酸盐 、 三氯氧磷 作用下， 反应 1.25h， 生成 2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  Sinnur, K. H.; Siddappa, S.; Hiremath, Shivayogi P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 894 - 896

  摘要：

  DOI：

文献信息

• Kamath, Pooja R.; Sunil, Dhanya; Ajees, A. Abdul, European Journal of Medicinal Chemistry, 2016, vol. 120, p. 134 - 147
  作者：Kamath, Pooja R.、Sunil, Dhanya、Ajees, A. Abdul、Pai、Biswas, Shubankar

  DOI：——

  日期：——
• SINNUR K. H.; SIDDAPPA S.; HIREMATH SHIVAYOGI P.; PUROHIT M. G., INDIAN J. CHEM., 25,(1986) N 9, 894-896
  作者：SINNUR K. H.、 SIDDAPPA S.、 HIREMATH SHIVAYOGI P.、 PUROHIT M. G.

  DOI：——

  日期：——