(2-indol-4-yl-ethyl)-methyl-amine | 94980-84-4

• 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: (2-indol-4-yl-ethyl)-methyl-amine
• 英文别名: [2-(1H-Indol-4-YL)ethyl](methyl)amine；2-(1H-indol-4-yl)-N-methylethanamine
• CAS: 94980-84-4
• 化学式: C₁₁H₁₄N₂
• 分子量: 174.246
• InChiKey: HBVLESSBJJJZFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (2-indol-4-yl-ethyl)-methyl-amine 在 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 4-Methyl-3,4,5,6-tetrahydro-1H-azepino[3,4,5-cd]indole
  参考文献：
  名称：

  1,9-Alkano-bridged 2,3,4,5-tetrahydro-1H-3-benzazepines with affinity for the .alpha.2-adrenoceptor and the 5-HT1A receptor

  摘要：

  A number of 1,9-alkano-bridged 2,3,4,5-tetrahydro-1H-3-benzazepines were prepared and evaluated for 5-HT1A receptor and alpha 2-adrenoceptor affinity by using radioligand receptor binding techniques. Several compounds displayed 5-HT1A receptor affinity comparable to, or greater than, the known 5-HT1A ligand buspirone. The highest affinity 5-HT1A receptor ligands were N-alkyl-, N-allyl-5-chloro-, and 5-methoxy-1,2,3,4,8,9,10,10a-octahydronaphth[1,8-cd]azapines (4c, 4m, 4n), which had pKi values of 7.9-8.1. The S enantiomer of 4c had a higher affinity for the 5-HT1A receptor than the corresponding R isomer (pKi of 8.2 for (S)-4c vs 7.7 for (R)-4c). These compounds had a relatively low affinity for the alpha 2-adrenoceptor (pKi of 7 or less). On the other hand, the closely related 5-chloro-2-methyl-2,3,4,8,9,9a-hexahydro-1H-indeno[1,7-cd]azepine (3b) had high affinity for both the alpha 2-adrenoceptor (pKi = 8.1) and 5-HT1A receptor (pKi = 7.6). These results indicate that the two receptors may share common recognition sites.

  DOI：

  10.1021/jm00164a026
• 作为产物：
  描述：

  N-[2-(1H-indol-4-yl)ethyl]formamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 16.0h， 生成 (2-indol-4-yl-ethyl)-methyl-amine
  参考文献：
  名称：

  1,9-Alkano-bridged 2,3,4,5-tetrahydro-1H-3-benzazepines with affinity for the .alpha.2-adrenoceptor and the 5-HT1A receptor

  摘要：

  A number of 1,9-alkano-bridged 2,3,4,5-tetrahydro-1H-3-benzazepines were prepared and evaluated for 5-HT1A receptor and alpha 2-adrenoceptor affinity by using radioligand receptor binding techniques. Several compounds displayed 5-HT1A receptor affinity comparable to, or greater than, the known 5-HT1A ligand buspirone. The highest affinity 5-HT1A receptor ligands were N-alkyl-, N-allyl-5-chloro-, and 5-methoxy-1,2,3,4,8,9,10,10a-octahydronaphth[1,8-cd]azapines (4c, 4m, 4n), which had pKi values of 7.9-8.1. The S enantiomer of 4c had a higher affinity for the 5-HT1A receptor than the corresponding R isomer (pKi of 8.2 for (S)-4c vs 7.7 for (R)-4c). These compounds had a relatively low affinity for the alpha 2-adrenoceptor (pKi of 7 or less). On the other hand, the closely related 5-chloro-2-methyl-2,3,4,8,9,9a-hexahydro-1H-indeno[1,7-cd]azepine (3b) had high affinity for both the alpha 2-adrenoceptor (pKi = 8.1) and 5-HT1A receptor (pKi = 7.6). These results indicate that the two receptors may share common recognition sites.

  DOI：

  10.1021/jm00164a026

文献信息

• Azepino- and Diazepinoindoles: Synthesis and Dopamine Receptor Binding Profiles
  作者：Johannes Kraxner、Harald H?bner、Peter Gmeiner

  DOI：10.1002/1521-4184(20009)333:9<287::aid-ardp287>3.0.co;2-r

  日期：2000.9

  available building blocks 7, 10, 11, and 15, the synthesis of the fused indoles 1, 2, 5, and 6, respectively, is reported. The syntheses involved Pictet‐Spengler cyclizations, Michael addition reactions, lactamization, directed metallation, and reductive amination as the key reaction steps. Radioligand displacement studies comprising the dopamine receptor subtypes D1, D2long D2short, D3, and D4.4 were

  从容易获得的构件 7、10、11 和 15 开始，分别报道了稠合吲哚 1、2、5 和 6 的合成。合成涉及 Pictet-Spengler 环化、迈克尔加成反应、内酰胺化、定向金属化和还原胺化作为关键反应步骤。当二氮杂吲哚 6 显示与部分 D1 激动剂 SKF 相当的 D1 和 D4 亲和力（分别为 Ki = 0.11 μM 和 1.7 μM）时，进行了包含多巴胺受体亚型 D1、D2long D2short、D3 和 D4.4 的放射性配体置换研究38393 (3b)。与苯并氮杂 3b 相比，基于吲哚的测试化合物对 D2 和 D3 受体亚型的选择性较低。
• Organic compounds
  申请人：Adcock Claire

  公开号：US20090215776A1

  公开（公告）日：2009-08-27

  Compounds of formula I in free or salt or solvate form, where T 1 , T 2 , X, R a , R b , R 8 and R 9 have the meanings as indicated in the specification, are useful for treating inflammatory or obstructive airways, pulmonary hypertension, pulmonary fibrosis, liver fibrosis, muscle diseases and systemic skeletal disorders. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.

  式I的化合物以自由形式、盐形式或溶剂合形式存在，其中T1、T2、X、Ra、Rb、R8和R9的含义如规范中所示，可用于治疗炎症或阻塞性气道、肺动脉高压、肺纤维化、肝纤维化、肌肉疾病和全身骨骼疾病。还描述了含有这些化合物的药物组合物和制备这些化合物的方法。
• Pyrimidine derivatives as alk-5 Inhibitors
  申请人：Leblanc Catherine

  公开号：US20090209539A1

  公开（公告）日：2009-08-20

  Compounds of formula (I) in free or salt or solvate form, where T 1 , T 2 , R a and R b have the meanings as indicated in the specification, are useful for treating inflammatory or obstructive airways, pulmonary hypertension, pulmonary fibrosis, liver fibrosis, muscle diseases and systemic skeletal disorders. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.

  式(I)的化合物以自由形式、盐形式或溶剂合形式存在，其中T1、T2、Ra和Rb的含义如说明书中所示，可用于治疗炎症或阻塞性呼吸道、肺动脉高压、肺纤维化、肝纤维化、肌肉疾病和系统性骨骼疾病。还描述了含有该化合物的制药组合物和制备该化合物的方法。
• PYRIMIDINE DERIVATIVES AS ALK-5 INHIBITORS
  申请人：Novartis AG

  公开号：EP2044056B1

  公开（公告）日：2012-08-22
• PYRIDINE DERIVATIVES
  申请人：Novartis AG

  公开号：EP2242742B1

  公开（公告）日：2015-12-02