N-[(1H-indole-3-yl)(phenyl)methyl]pyrimidine-2-amine | 1258955-52-0

• 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: N-[(1H-indole-3-yl)(phenyl)methyl]pyrimidine-2-amine
• 英文别名: N-[1H-indol-3-yl(phenyl)methyl]pyrimidin-2-amine
• CAS: 1258955-52-0
• 化学式: C₁₉H₁₆N₄
• 分子量: 300.363
• InChiKey: DXBKQECOHIUAEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3,5-三嗪-2,4,6-三胺,N,N'''-1,2-乙二基二[N-[3-[[4,6-二[丁基(2,2,6,6-四甲基-4-哌啶基)氨基]-1,3,5-三嗪-2-基]氨基]丙基]-N,N''-二丁基-N,N''-二(2,2,6,6-四甲基-4-哌啶基)- 、 吲哚 、 苯甲醛 反应 3.0h， 以90%的产率得到N-[(1H-indole-3-yl)(phenyl)methyl]pyrimidine-2-amine
  参考文献：
  名称：

  N -[（1 H-吲哚-3-基）芳基甲基]杂芳基胺的简单无溶剂绿色合成

  摘要：

  在无溶剂条件下，吲哚，芳族醛和杂芳基胺的一锅三组分偶联反应可导致以中等至高收率形成相应的新型3-[（N-杂芳基）（芳基）甲基]吲哚。这种多组分反应的关键特征是反应过程简单，无需有机溶剂或酸催化剂，无需进一步纯化即可轻松分离产物。

  DOI：

  10.1016/j.tetlet.2010.07.175

文献信息

• A simple, solvent and catalyst-free green synthesis of novel N-[(1H-indol-3-yl)arylmethyl]heteroarylamines
  作者：Abolfazl Olyaei、Bahareh Shams、Mahdieh Sadeghpour、Fatemeh Gesmati、Zeinab Razaziane

  DOI：10.1016/j.tetlet.2010.07.175

  日期：2010.11

  One-pot, three-component coupling reactions of indole, aromatic aldehydes, and heteroaryl amines under solvent-free conditions lead to the formation of the corresponding novel 3-[(N-heteroaryl)(aryl)methyl]indoles in moderate to high yields. The key features of this multi-component reaction are the simple reaction procedure, no organic solvent or acid catalyst, and easy product separation without further

  在无溶剂条件下，吲哚，芳族醛和杂芳基胺的一锅三组分偶联反应可导致以中等至高收率形成相应的新型3-[（N-杂芳基）（芳基）甲基]吲哚。这种多组分反应的关键特征是反应过程简单，无需有机溶剂或酸催化剂，无需进一步纯化即可轻松分离产物。
• 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.