N-(cyclohexylmethyl)-4-methoxy-N-(3-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)propyl)benzenesulfonamide | 1220707-00-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N-(cyclohexylmethyl)-4-methoxy-N-(3-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)propyl)benzenesulfonamide
• 英文别名: N-(cyclohexylmethyl)-4-methoxy-N-[3-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propyl]benzenesulfonamide
• CAS: 1220707-00-5
• 化学式: C₂₈H₃₈F₃N₃O₃S
• 分子量: 553.689
• InChiKey: XRFNGTPQLMHMKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  61.5
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  N-(cyclohexylmethyl)-3-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)propan-1-amine 、 对甲氧基苯磺酰氯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 以58%的产率得到N-(cyclohexylmethyl)-4-methoxy-N-(3-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)propyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and biological evaluation of (phenylpiperazinyl-propyl)arylsulfonamides as selective 5-HT2A receptor antagonists

  摘要：

  A novel series of 5-HT2A ligands that contain a (phenylpiperazinyl-propyl)arylsulfonamides skeleton was synthesized. Thirty-seven N-(cycloalkylmethyl)-4-methoxy-N-(3-(4-arylpiperazin-1-yl)propyl)arylsulfonamide and N-(4-(4-arylpiperazin-1-yl)butan-2-yl)-arylsulfonamide compounds were obtained. The binding of these compounds to the 5-HT2A, 5-HT2C, and 5-HT7 receptors was evaluated. Most of the compounds showed IC50 values of less than 100 nM and exhibited high selectivity for the 5-HT2A receptor. Among the synthesized compounds, 16a and 16d showed good affinity at 5-HT2A (IC50 = 0.7 nM and 0.5 nM) and good selectivity over 5-HT2C (50-100 times) and 5-HT7 (1500-3000 times). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.067

文献信息

• Synthesis and biological evaluation of (phenylpiperazinyl-propyl)arylsulfonamides as selective 5-HT2A receptor antagonists
  作者：Euna Yoo、Juhee Yoon、Ae Nim Pae、Hyewhon Rhim、Woo-Kyu Park、Jae Yang Kong、Hea-Young Park Choo

  DOI：10.1016/j.bmc.2009.12.067

  日期：2010.2

  A novel series of 5-HT2A ligands that contain a (phenylpiperazinyl-propyl)arylsulfonamides skeleton was synthesized. Thirty-seven N-(cycloalkylmethyl)-4-methoxy-N-(3-(4-arylpiperazin-1-yl)propyl)arylsulfonamide and N-(4-(4-arylpiperazin-1-yl)butan-2-yl)-arylsulfonamide compounds were obtained. The binding of these compounds to the 5-HT2A, 5-HT2C, and 5-HT7 receptors was evaluated. Most of the compounds showed IC50 values of less than 100 nM and exhibited high selectivity for the 5-HT2A receptor. Among the synthesized compounds, 16a and 16d showed good affinity at 5-HT2A (IC50 = 0.7 nM and 0.5 nM) and good selectivity over 5-HT2C (50-100 times) and 5-HT7 (1500-3000 times). (C) 2010 Elsevier Ltd. All rights reserved.