N-ethyl-N-(3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl)amine | 793672-13-6

• 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-ethyl-N-(3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl)amine
• 英文别名: N-ethyl-3-[4-(2-methoxyphenyl)piperazin-1-yl]propan-1-amine
• CAS: 793672-13-6
• 化学式: C₁₆H₂₇N₃O
• 分子量: 277.41
• InChiKey: LDPZMJOTOBMABX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  27.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-ethyl-N-(3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl)amine 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 N-ethyl-N-(3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl)-6-quinolinesulfonamide hydrochloride
  参考文献：
  名称：

  Arene- and quinoline-sulfonamides as novel 5-HT7 receptor ligands

  摘要：

  Novel arene- and quinolinesulfonamides were synthesized using different solutions and a solid-support methodology, and were evaluated for their affinity for 5-HT1A, 5-HT2A, 5-HT6, and 5-HT7 receptors. Compound 54 (N-Ethyl-N-[4-(1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinolin-2-yl)butyl]-8-quinolinesulfonamide) was identified as potent 5-HT7 antagonist (K-i = 13 nM, K-B = 140 nM) with good selectivity over 5-HT1A, 5-HT2A, 5-HT6 receptors. In the FST in mice, it reduced immobility in a manner similar to the selective 5-HT7 antagonist SB-269970. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.044
• 作为产物：
  描述：

  3-[4-(2-methoxyphenyl)piperazin-1-yl]propionitrile 在 lithium aluminium tetrahydride 、 三氯化铝 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-ethyl-N-(3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl)amine
  参考文献：
  名称：

  Novel 5-HT₇ Receptor Inverse Agonists. Synthesis and Molecular Modeling of Arylpiperazine- and 1,2,3,4-Tetrahydroisoquinoline-Based Arylsulfonamides

  摘要：

  A series of arylpiperazine- and 1,2,3,4-tetrahydroisoquinoline-based arylsulfonamides was synthesized and evaluated for their interactions with the constitutively active 5-HT7 receptor. Effects on basal adenylate cyclase activity were measured using HEK-293 cells expressing the rat 5-HT7. All ligands produced a decrease of adenylate cyclase activity, indicative of their inverse agonism. Additionally, computational studies with a set of 22 inverse agonists, including these novel inverse agonists and inverse agonists known from literature, resulted in a pharmacophore model and a CoMFA model (R-2 = 0.97, SE = 0.18). Docking of inverse agonists at the binding site of a model of the helical parts of the 5-HT7 receptor, based on the a carbon template for 7-TM GPCRs, revealed interesting molecular interactions and a possible explanation for observed structure-activity relationships.

  DOI：

  10.1021/jm049743b