3-((4-methoxyphenyl)(pyrrolidin-1-yl)methyl)-1H-indole | 1609026-89-2

• 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-((4-methoxyphenyl)(pyrrolidin-1-yl)methyl)-1H-indole
• 英文别名: 3-[(4-methoxyphenyl)-pyrrolidin-1-ylmethyl]-1H-indole
• CAS: 1609026-89-2
• 化学式: C₂₀H₂₂N₂O
• 分子量: 306.407
• InChiKey: JRZKKYYPQOMHNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  28.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 吲哚 、 4-甲氧基苯甲醛 以 乙二醇 为溶剂， 以88%的产率得到3-((4-methoxyphenyl)(pyrrolidin-1-yl)methyl)-1H-indole
  参考文献：
  名称：

  通过曼尼希型反应无催化剂和多组分合成 3-氨基烷基化吲哚：多靶点抗癌、酪氨酸酶和 α-葡萄糖苷酶抑制活性

  摘要：

  以甲醇和乙二醇 (EG) 作为促进介质，在无催化剂条件下通过曼尼希型反应研究了一种高效且可持续的 3-氨基烷基化吲哚多组分合成方法。无需柱层析即可合成各种底物，省时、方便，是该方法的优点之一。此外，本研究还考虑了环境友好性。通过光谱分析证实合成的吲哚衍生物4a-g和5a-g进行了体外研究对人癌细胞系如肺癌 (A549)、乳腺癌 (MDA-MB-231) 和前列腺 (PC3) 的抗癌活性以及它们的抗酪氨酸酶和 α-葡萄糖苷酶抑制活性。具体而言，结果表明，大多数合成的吲哚均抑制癌细胞系和腺癌细胞系，并以相同的方式影响对所有三种癌细胞系的细胞毒活性；此外，化合物5e和5f被证明是多靶点抗癌剂。分子对接研究的结果表明，最有效的化合物5e和5f与 TopI-DNA 结合位点的结合是通过氢键和疏水相互作用进行的，与喜树碱结合相当。

  DOI：

  10.1039/d1nj02536h

文献信息

• Natural Products for Drug Discovery: Discovery of Gramines as Novel Agents against a Plant Virus
  作者：Aidang Lu、Tienan Wang、Hao Hui、Xiaoye Wei、Weihao Cui、Chunlv Zhou、Hongyan Li、Ziwen Wang、Jincheng Guo、Dejun Ma、Qingmin Wang

  DOI：10.1021/acs.jafc.8b06859

  日期：2019.2.27

  Plant viral diseases seriously affect crop yield and quality. The natural product gramine (1) and its simple structural analogues 2-35 were synthesized from indoles, amines, and aldehydes in one step. The antiviral effects of these alkaloids were evaluated systematically. Most of these compounds were found to have higher antiviral effects than commercial ribavirin for the first time. Especially compounds 22, 30, and 31 exhibited significantly higher effects than ningnanmycin, thereby emerging as novel antiviral leads for further optimization. The preliminary implementation indicated that these compounds likely inhibit the assembly of tobacco mosaic virus (TMV) by cross-linking TMV capsid protein. Gramine analogues were also found to have broad-spectrum fungicidal effects. Although gramine has been reported to have influence on germination and development of Erysiphe graminis, these compounds displayed no fungicidal effects against Blumeria graminis f. sp. tritici on wheat in our test. Some of these compounds also exhibited certain insecticidal activities.
• Catalyst-free, ethylene glycol promoted one-pot three component synthesis of 3-amino alkylated indoles via Mannich-type reaction
  作者：U. Chinna Rajesh、Rohit Kholiya、V. Satya Pavan、Diwan S. Rawat

  DOI：10.1016/j.tetlet.2014.03.112

  日期：2014.4

  A highly efficient and sustainable approach for the multi-component synthesis of biologically important 3-amino alkylated indoles has been investigated via Mannich-type reaction under catalyst-free, ethylene glycol as a recyclable promoting medium. The wide applicability of the present method was examined with various substrates viz substituted aldehydes, indoles and secondary amines. This method will be useful for a large scale synthesis of 3-amino alkylated indoles without the use of column chromatography. The present method provides higher environmental compatibility and sustainability factors such as smaller E-factor (0.433) and higher atom-economy (AE = 93.3%). (C) 2014 Elsevier Ltd. All rights reserved.