5-chloro-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide | 1377838-16-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 5-chloro-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide
• 英文别名: 5-chloro-N-(2-(4-(piperidin-1-yl)phenyl)ethyl)-1H-indole-2-carboxamide；5-chloro-N-[2-(4-piperidin-1-ylphenyl)ethyl]-1H-indole-2-carboxamide
• CAS: 1377838-16-8
• 化学式: C₂₂H₂₄ClN₃O
• 分子量: 381.905
• InChiKey: PZDXLVPRWYKHPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  48.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氨基苯乙腈 在 lithium aluminium tetrahydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 生成 5-chloro-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide
  参考文献：
  名称：

  Design, synthesis and pharmacophoric model building of new 3-alkoxymethyl/3-phenyl indole-2-carboxamides with potential antiproliferative activity

  摘要：

  Novel 3‐alkoxymethyl/3‐phenyl indole‐2‐carboxamide derivatives were synthesized and evaluated for their anticancer activity. Most of the tested compounds showed moderate to excellent activity against the tested cell lines (MCF7 and HCT116). 3‐Phenyl substitution on indole with p‐piperidinyl phenethyl 24a and p‐dimethylamino phenethyl 24c exhibited anticancer activity against MCF7 with IC50 of 0.13 and 0.14 μm, respectively. Further mechanistic study of the most active compounds through their action on cell cycle showed disturbance in cell cycle progression and cell cycle arrest. For future development of this series of compounds, pharmacophore study was conducted which indicated that the enhancement of the activity could be achieved through the addition of acceptor or donating groups to the already‐present indole nucleus.

  DOI：

  10.1111/cbdd.12928

文献信息

• Indole-2-carboxamides as Allosteric Modulators of the Cannabinoid CB₁ Receptor
  作者：Francesco Piscitelli、Alessia Ligresti、Giuseppe La Regina、Antonio Coluccia、Ludovica Morera、Marco Allarà、Ettore Novellino、Vincenzo Di Marzo、Romano Silvestri

  DOI：10.1021/jm201485c

  日期：2012.6.14

  We synthesized new N-phenylethyl-1H-indole-2-carboxamides as the first SAR study of allosteric modulators of the CB1 receptor. The presence of the carboxamide functionality was required in order to obtain a stimulatory effect. The maximum stimulatory activity on CB1 was exerted by carboxamides 13 (EC50 = 50 nM) and 21 (EC50 = 90 nM) bearing a dimethylamino or piperidinyl group, respectively, at position

  我们合成了新的N-苯乙基-1 H-吲哚-2-羧酰胺作为CB 1受体的变构调节剂的第一个SAR研究。为了获得刺激作用，需要羧酰胺官能团的存在。CB 1的最大刺激活性是由分别在苯乙部分的4位带有二甲氨基或哌啶基的羧酰胺13（EC 50 = 50 nM）和21（EC 50 = 90 nM）发挥的。吲哚的5。
• Design, synthesis and pharmacophoric model building of new 3-alkoxymethyl/3-phenyl indole-2-carboxamides with potential antiproliferative activity
  作者：Mostafa H. Abdelrahman、Ahmed S. Aboraia、Bahaa G. M. Youssif、Bakheet E. M. Elsadek

  DOI：10.1111/cbdd.12928

  日期：2017.7

  Novel 3‐alkoxymethyl/3‐phenyl indole‐2‐carboxamide derivatives were synthesized and evaluated for their anticancer activity. Most of the tested compounds showed moderate to excellent activity against the tested cell lines (MCF7 and HCT116). 3‐Phenyl substitution on indole with p‐piperidinyl phenethyl 24a and p‐dimethylamino phenethyl 24c exhibited anticancer activity against MCF7 with IC50 of 0.13 and 0.14 μm, respectively. Further mechanistic study of the most active compounds through their action on cell cycle showed disturbance in cell cycle progression and cell cycle arrest. For future development of this series of compounds, pharmacophore study was conducted which indicated that the enhancement of the activity could be achieved through the addition of acceptor or donating groups to the already‐present indole nucleus.