(4-chlorophenyl)(4-(2-((3-isopropylisoxazol-5-ylmethyl)amino)ethyl)piperazin-1-yl)methanone | 1355016-37-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-chlorophenyl)(4-(2-((3-isopropylisoxazol-5-ylmethyl)amino)ethyl)piperazin-1-yl)methanone
• 英文别名: (4-Chlorophenyl)-[4-[2-[(3-propan-2-yl-1,2-oxazol-5-yl)methylamino]ethyl]piperazin-1-yl]methanone
• CAS: 1355016-37-3
• 化学式: C₂₀H₂₇ClN₄O₂
• 分子量: 390.913
• InChiKey: USQNPVLXAIUWBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-(4-氯苯甲酰基)哌嗪-1-羧酸叔丁酯 在 三乙酰氧基硼氢化钠 、 potassium carbonate 、 一水合肼 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 39.0h， 生成 (4-chlorophenyl)(4-(2-((3-isopropylisoxazol-5-ylmethyl)amino)ethyl)piperazin-1-yl)methanone
  参考文献：
  名称：

  4-Aminoethylpiperazinyl aryl ketones with 5-HT1A/5-HT7 selectivity

  摘要：

  The well-known 5-HT1A/5-HT7 selectivity issue was tackled by a new series of 4-aminoethylpiperazinyl aryl ketones (1a-1l) specifically designed to distinguish the two hydrophobic sites centered at the anchoring salt bridge. The 4-aminoethylpiperazinyl aryl ketones showed a wide spectrum of activity and selectivity for the 5-HT receptors depending on the type of the hydrophobic groups attached at the aryl piperazinyl ketone scaffold. Docking study of the most active compounds against 5-HT7R and 5-HT1AR revealed that both receptors have two hydrophobic pockets around the anchoring salt bridge. These two binding sites are perpendicular to each other in 5-HT7R but parallel in 5-HT1AR, and this observation is well matched with the previous report which claimed that 5-HT7R affinity arises from bent conformation of the bound ligand whereas an extended one is best suited for 5-HT1AR selectivity. Also, as these pockets have different size and shape, inhibitory activity as well as selectivity of the 4-aminoethylpiperazinyl aryl ketones against 5-HT7R and 5-HT1AR seemed to be determined by combination of two hydrophobic substituents attached at both ends of the title compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.005

文献信息

• 4-Aminoethylpiperazinyl aryl ketones with 5-HT1A/5-HT7 selectivity
  作者：Mi Kyoung Kim、Hyo Seon Lee、Sora Kim、Suh Young Cho、Bryan L. Roth、Youhoon Chong、Hyunah Choo

  DOI：10.1016/j.bmc.2011.11.005

  日期：2012.1

  The well-known 5-HT1A/5-HT7 selectivity issue was tackled by a new series of 4-aminoethylpiperazinyl aryl ketones (1a-1l) specifically designed to distinguish the two hydrophobic sites centered at the anchoring salt bridge. The 4-aminoethylpiperazinyl aryl ketones showed a wide spectrum of activity and selectivity for the 5-HT receptors depending on the type of the hydrophobic groups attached at the aryl piperazinyl ketone scaffold. Docking study of the most active compounds against 5-HT7R and 5-HT1AR revealed that both receptors have two hydrophobic pockets around the anchoring salt bridge. These two binding sites are perpendicular to each other in 5-HT7R but parallel in 5-HT1AR, and this observation is well matched with the previous report which claimed that 5-HT7R affinity arises from bent conformation of the bound ligand whereas an extended one is best suited for 5-HT1AR selectivity. Also, as these pockets have different size and shape, inhibitory activity as well as selectivity of the 4-aminoethylpiperazinyl aryl ketones against 5-HT7R and 5-HT1AR seemed to be determined by combination of two hydrophobic substituents attached at both ends of the title compounds. (C) 2011 Elsevier Ltd. All rights reserved.