N-[2-[4-(3-chlorophenyl)-1-piperazinyl]ethyl]-N'-tricyclo[3.3.1.1(3,7)]dec-1-ylurea

• 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-[2-[4-(3-chlorophenyl)-1-piperazinyl]ethyl]-N'-tricyclo[3.3.1.1(3,7)]dec-1-ylurea
• 英文别名: 1-Adamantan-1-yl-3-{2-[4-(3-chloro-phenyl)-piperazin-1-yl]-ethyl}-urea；1-(1-adamantyl)-3-[2-[4-(3-chlorophenyl)piperazin-1-yl]ethyl]urea
• 化学式: C₂₃H₃₃ClN₄O
• 分子量: 416.994
• InChiKey: YNPAKXJCEFCUJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  47.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  盐酸金刚烷胺 、 2-[4-(3-氯苯基)哌嗪-1-基]乙胺 、 氯甲酸三氯甲酯 在 三乙胺 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 N-[2-[4-(3-chlorophenyl)-1-piperazinyl]ethyl]-N'-tricyclo[3.3.1.1(3,7)]dec-1-ylurea
  参考文献：
  名称：

  Polycyclic-carbamic acid piperazinoalkyl esters and amides

  摘要：

  该公式化合物为：##STR1## 其中Ad是1-金刚烷基、2-金刚烷基或3-去金刚烷基；X为--O--或##STR2## n为1、2、3或4；R.sup.1和R.sup.2分别为氢、烷基、苯基、苄基或取代苯基或苄基，其中取代基为烷基、烷氧基、卤素、氰基、硝基或三氟甲基；R.sup.3为苯基、苄基或取代苯基或苄基，其中取代基为烷基、烷氧基、卤素、硝基、氰基或全氟甲基，2-、3-或4-吡啶基、2-、4-或5-吡咯啉基；或2-或3-吡嗪基；R.sup.4和R.sup.5分别为氢、甲基、苯基或苄基；或其药学上可接受的盐，可用作抗焦虑/抗抑郁药物，具有抗精神病活性成分。

  公开号：

  US04882432A1

文献信息

• Polycyclic-carbamic acid piperazinoalkyl esters and amides
  申请人：American Home Products Corporation

  公开号：US04882432A1

  公开（公告）日：1989-11-21

  The compounds of the formula: ##STR1## wherein Ad is 1-adamantyl, 2-adamantyl or 3-noradamantyl; X is --O-- or ##STR2## n is 1,2,3 or 4; R.sup.1 and R.sup.2 are, independently, hydrogen, alkyl, phenyl, benzyl, or substituted phenyl or benzyl in which the substituent is alkyl, alkoxy, halo, cyano, nitro or trifluoromethyl; and R.sup.3 is phenyl, benzyl or substituted phenyl or benzyl in which the substituent is alkyl, alkoxy, halo, nitro, cyano or perhalomethyl, 2-, 3-, or 4-pyridinyl, 2-, 4-or 5-pyrimidiny; or 2- or 3-pyrazinyl; R.sup.4 and R.sup.5 are independently, hydrogen, methyl, phenyl or benzyl; or a pharmaceutically acceptable salt thereof, are useful anxiolytic/antidepressant agents, with elements of antipsychotic activity.

  该公式化合物为：##STR1## 其中Ad是1-金刚烷基、2-金刚烷基或3-去金刚烷基；X为--O--或##STR2## n为1、2、3或4；R.sup.1和R.sup.2分别为氢、烷基、苯基、苄基或取代苯基或苄基，其中取代基为烷基、烷氧基、卤素、氰基、硝基或三氟甲基；R.sup.3为苯基、苄基或取代苯基或苄基，其中取代基为烷基、烷氧基、卤素、硝基、氰基或全氟甲基，2-、3-或4-吡啶基、2-、4-或5-吡咯啉基；或2-或3-吡嗪基；R.sup.4和R.sup.5分别为氢、甲基、苯基或苄基；或其药学上可接受的盐，可用作抗焦虑/抗抑郁药物，具有抗精神病活性成分。
• US4882432A
  申请人：——

  公开号：US4882432A

  公开（公告）日：1989-11-21
• Synthesis and SAR of Adatanserin:  Novel Adamantyl Aryl- and Heteroarylpiperazines with Dual Serotonin 5-HT_1A and 5-HT₂ Activity as Potential Anxiolytic and Antidepressant Agents
  作者：Magid A. Abou-Gharbia、Wayne E. Childers、Horace Fletcher、Georgia McGaughey、Usha Patel、Michael B. Webb、John Yardley、Terrance Andree、Carl Boast、Robert J. Kucharik、Karen Marquis、Herman Morris、Rosemary Scerni、John A. Moyer

  DOI：10.1021/jm9806704

  日期：1999.12.1

  Several novel functionalized adamantyl aryl- and heteroarylpiperazine derivatives were prepared and examined in various receptor binding and behavioral tests to determine their serotonin receptor activities. Many compounds demonstrated modest to high affinity for 5-HT1A receptors, with compounds 9, 13, 23, 33, 34, and 43 being the most potent at this site. Compound 1, 2-[4-(2-pyrimidinyl)-1-piperazinyl] ethyl adamantyl-1-carboxylate, demonstrated relatively high affinity for 5-HT1A receptors (K-i = 8 nM) and acceptable selectivity versus D-2 receptors (K-i = 708 mM); however, it lacked in vivo activity in serotonergic behavioral models. In contrast, compounds 9 (WY-50,324, SEB-324, adatanserin), adamantyl-1-carboxylic acid 2-[4-(2-pyrimidinyl)-1-piperazinyl]ethylamide, and 13, adamantyl-1-carboxylic acid 2-[4-(2-methoxyphenyl)-1-piperazinyl] ethylamide, demonstrated high affinity for 5-HT1A binding sites (K-i = 1 nM for both) and moderate affinity for 5-HT2 receptors (K-i = 73 and 75 nM, respectively). Both compounds also demonstrated partial 5-HT1A agonist activity in vivo in rat serotonin syndrome and 5-HT2 antagonist activity in quipazine- and DOI-induced head shake paradigms. The selective 5-HT1A partial agonist and 5-HT2 antagonist activity of 9 was accompanied by significant anxiolytic activity in an animal conflict model. On the basis of this profile, compound 9 entered development as a combined anxiolytic and antidepressant agent.