2-Methyl-3-piperidinomethyl-indol | 4071-15-2

• 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: 2-Methyl-3-piperidinomethyl-indol
• 英文别名: 2-methyl-3-piperidinomethyl-indole；2-Methyl-3-(1-piperidinylmethyl)-1h-indole；2-methyl-3-(piperidin-1-ylmethyl)-1H-indole
• CAS: 4071-15-2
• 化学式: C₁₅H₂₀N₂
• 分子量: 228.337
• InChiKey: WLTYXHKAKNGEJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Methyl-3-piperidinomethyl-indol 在 乙醇 、 硫酸二甲酯 作用下， 生成 2-(2-methyl-indol-3-ylmethyl)-cyclohexanone
  参考文献：
  名称：

  Plieninger, Chemische Berichte, 1953, vol. 86, p. 404,409

  摘要：

  DOI：
• 作为产物：
  描述：

  哌啶 、 2-甲基吲哚 、 二氯甲烷 以 甲醇 为溶剂， 50.0 ℃ 、800.0 MPa 条件下， 反应 48.0h， 以7%的产率得到2-Methyl-3-piperidinomethyl-indol
  参考文献：
  名称：

  Mannich Reactions of Indoles with Dichloromethane and Secondary Amines under High Pressure

  摘要：

  Mannich reactions of indole with dichloromethane and secondary amines gave the corresponding Mannich bases in moderate to good yields, while 2-methylindole afforded only low yields of the Mannich bases. Some limitations were observed in the cases of hindered amines and 2-phenylindole.

  DOI：

  10.3987/com-93-6451

文献信息

• Lead Optimization Studies of Cinnamic Amide EP2 Antagonists
  作者：Thota Ganesh、Jianxiong Jiang、Myung-Soon Yang、Ray Dingledine

  DOI：10.1021/jm5000672

  日期：2014.5.22

  Prostanoid receptor EP2 can play a proinflammatory role, exacerbating disease pathology in a variety of central nervous system and peripheral diseases. A highly selective EP2 antagonist could be useful as a drug to mitigate the inflammatory consequences of EP2 activation. We recently identified a cinnamic amide class of EP2 antagonists. The lead compound in this class (5d) displays anti-inflammatory and neuroprotective actions. However, this compound exhibited moderate selectivity to EP2 over the DP1 prostanoid receptor (similar to 10-fold) and low aqueous solubility. We now report compounds that display up to 180-fold selectivity against DP1 and up to 9-fold higher aqueous solubility than our previous lead. The newly developed compounds also display higher selectivity against EP4 and IP receptors and a comparable plasma pharmacokinetics. Thus, these compounds are useful for proof of concept studies in a variety of models where EP2 activation is playing a deleterious role.
• THE PREPARATION OF MANNICH BASES RELATED TO GRAMINE
  作者：WARREN J. BREHM、H. G. LINDWALL

  DOI：10.1021/jo01149a039

  日期：1950.5
• [EN] COMPOUNDS BASED ON FOUR AROMATIC RINGS, PREPARATION AND USES THEREOF<br/>[FR] COMPOSES A BASE DE QUATRE CYCLES AROMATIQUES, PREPARATION ET UTILISATIONS
  申请人：CEREP

  公开号：WO2007071840A2

  公开（公告）日：2007-06-28

  [EN] The present invention relates to novel compounds, to the preparation thereof and to uses, in particular therapeutic uses, thereof. It relates more particularly to derived compounds which have at least four aromatic rings, to the preparation thereof and to uses thereof, in particular in the field of human or animal health. These compounds have in particular a certain affinity for neuropeptide Y, NPY, biological receptors, and more particularly for NPY Y1 receptors, present in the central and peripheral nervous systems. The compounds according to the invention are preferably NPY antagonists, and can therefore be used in the therapeutic or prophylactic treatment of any disorder involving NPY. The present invention also relates to pharmaceutical compositions comprising such compounds, to the preparation thereof and to uses thereof, and also to methods of treatment using said compounds.
  [FR] La présente invention concerne de nouveaux composés, leur préparation et leurs utilisations, notamment thérapeutiques. Elle concerne plus particulièrement des composés dérivés présentant au moins quatre cycles aromatiques, leur préparation et leurs utilisations, notamment dans le domaine de la santé humaine ou animale. Ces composés ont en particulier une certaine affinité pour les récepteurs biologiques du neuropeptide Y, NPY et plus particulièrement pour les récepteurs NPY Yl, présents dans les systèmes nerveux central et périphérique. Les composés selon l'invention sont préférentiellement des antagonistes de NPY, et sont donc utilisables dans le traitement thérapeutique ou prophylactique de tout désordre impliquant NPY. La présente invention concerne également des compositions pharmaceutiques comprenant de tels composés, leur préparation et leurs utilisations, ainsi que des méthodes de traitement utilisant lesdits composés.
• Plieninger, Chemische Berichte, 1953, vol. 86, p. 404,409
  作者：Plieninger

  DOI：——

  日期：——
• Mannich Reactions of Indoles with Dichloromethane and Secondary Amines under High Pressure
  作者：Kiyoshi Matsumoto、Takane Uchida、Shiro Hashimoto、Yukie Yonezawa、Hirokazu Iida、Akikazu Kakehi、Shinichi Otani

  DOI：10.3987/com-93-6451

  日期：——

  Mannich reactions of indole with dichloromethane and secondary amines gave the corresponding Mannich bases in moderate to good yields, while 2-methylindole afforded only low yields of the Mannich bases. Some limitations were observed in the cases of hindered amines and 2-phenylindole.