N-((1H-indol-3-yl)(4-trifluoromethylphenyl)methyl)pyridin-2-amine | 1393904-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-((1H-indol-3-yl)(4-trifluoromethylphenyl)methyl)pyridin-2-amine
• 英文别名: N-[1H-indol-3-yl-[4-(trifluoromethyl)phenyl]methyl]pyridin-2-amine
• CAS: 1393904-08-9
• 化学式: C₂₁H₁₆F₃N₃
• 分子量: 367.373
• InChiKey: RYQQXLTVWDTZSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  40.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 吲哚 、 对三氟甲基苯甲醛 以86%的产率得到N-((1H-indol-3-yl)(4-trifluoromethylphenyl)methyl)pyridin-2-amine
  参考文献：
  名称：

  Heterocycle-functional gramine analogues: Solvent- and catalyst-free synthesis and their inhibition activities against cell proliferation

  摘要：

  A series of novel gramine analogues were designed and synthesized via a convenient three-component reaction, and which were evaluated for their inhibition activities against cell proliferation. Their structures were confirmed by satisfactory spectra analyses mainly including H-1 NMR, and ESI-MS analyses. The preliminary assays indicated that some of the newly synthesized compounds displayed significantly good inhibition activities against human lung cancer (NCI-H460), hepatocellular liver carcinoma (HepG2), gastric cancer (SGC-7901 and BGC-823) cell lines compared with the control 5-Fluorouracil (5-FU), which might be developed as novel lead scaffold for potential anticancer agents. (c) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.003

文献信息

• Heterocycle-functional gramine analogues: Solvent- and catalyst-free synthesis and their inhibition activities against cell proliferation
  作者：Shaoyong Ke、Liqiao Shi、Xiufang Cao、Qingyu Yang、Ying Liang、Ziwen Yang

  DOI：10.1016/j.ejmech.2012.05.003

  日期：2012.8

  A series of novel gramine analogues were designed and synthesized via a convenient three-component reaction, and which were evaluated for their inhibition activities against cell proliferation. Their structures were confirmed by satisfactory spectra analyses mainly including H-1 NMR, and ESI-MS analyses. The preliminary assays indicated that some of the newly synthesized compounds displayed significantly good inhibition activities against human lung cancer (NCI-H460), hepatocellular liver carcinoma (HepG2), gastric cancer (SGC-7901 and BGC-823) cell lines compared with the control 5-Fluorouracil (5-FU), which might be developed as novel lead scaffold for potential anticancer agents. (c) 2012 Elsevier Masson SAS. All rights reserved.
• 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.