3-(3,4-dimethoxyphenyl)-3-(1H-indol-3-yl)-1-phenylpropan-1-one | 71710-51-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(3,4-dimethoxyphenyl)-3-(1H-indol-3-yl)-1-phenylpropan-1-one
• 英文别名: 3-(3,4-dimethoxy-phenyl)-3-indol-3-yl-1-phenyl-propan-1-one；1-Phenyl-3-<3>indolyl-3-(3,4-dimethoxyphenyl)-propanon-(1)
• CAS: 71710-51-5
• 化学式: C₂₅H₂₃NO₃
• 分子量: 385.463
• InChiKey: FUBXNYXBQKMPAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚 以52%的产率得到
  参考文献：
  名称：

  KOHOHOBA B. B.; CEMEHOB A. A., IZV. SIB. OTD. AN CCCP. CEP. XIM. N., 1979, HO 7-3, 147-150

  摘要：

  DOI：

文献信息

• Br2 as a novel Lewis acid catalyst for Friedel–Crafts alkylation of indoles with α,β-unsaturated ketones
  作者：Deqiang Liang、Xiangguang Li、Wanshun Zhang、Yanni Li、Mi Zhang、Ping Cheng

  DOI：10.1016/j.tetlet.2016.01.078

  日期：2016.3

  The inexpensive Br2 can serve as a novel Lewis acid catalyst for Friedel–Crafts alkylation of indoles with α,β-unsaturated ketones. Under the catalysis of only 3 mol % of Br2, this Michael addition proceeded smoothly with high efficiency and broad substrate scope. Moreover, theoretical calculations suggested that Br2 possesses only the modest power to activate chalcones and is inferior to most tested

  廉价的Br 2可以用作新颖的路易斯酸催化剂，用于用α，β-不饱和酮对吲哚进行Friedel-Crafts烷基化。在仅3mol％的Br 2的催化下，该迈克尔加成反应以高效率和宽泛的底物范围顺利进行。此外，理论计算表明，Br 2仅具有适度的活化查耳酮的能力，并且不如大多数测试的酸，这表明酸度可能不是当前通讯中Br 2独特活性的主要原因。
• Synthesis and in vitro cytotoxicity study of 3-(1H-indol-3-yl)-1,3-diphenylpropan-1-ones
  作者：Jagadeesh N. Masagalli、Kittappa M. Mahadevan、Honnali Jayadevappa、Hosanagara N. Harishkumar、Rajesha Ganalu、Prashantha Nagaraja

  DOI：10.1007/s00044-013-0875-y

  日期：2014.6

  A series of 3-(1H-indol-3-yl)-1,3-diphenylpropan-1-ones 3a-l were synthesized in good to excellent yield by Michael addition of indole 1 with alpha,beta-unsaturated ketones 2a-l in presence of indium(III) sulphate (20 mol%). The structure of the title compounds were established by H-1 NMR, C-13 NMR, mass and elemental analysis. All the synthesized compounds were evaluated for in vitro cytotoxicity against five different cancer cell lines such as ACHN (human kidney adenocarcinoma), Panc1 (pancreatic), Calu1 (lung), H460 (non small cell lung), HCT116 (human colon cancer cell) and MCF10A (normal breast epithelium) using propidium iodide staining assay protocol. The result showed that the compounds 3e and 3l have excellent cytotoxic activity with the IC50 value ranging from 1.4-2.7 to 2.4-3.4 mu M, respectively, in comparison with the other compounds, Flavopiridol and Gemcitabine were employed as a positive control. The findings conferred 3-(1H-indol-3-yl)-1,3-diphenylpropan-1-ones seem to be promising candidates for the development of new anticancer drugs.