3-[4-(3-trifluoromethylphenyl)-1-piperazinyl]propanol | 32212-47-8

• 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: 3-[4-(3-trifluoromethylphenyl)-1-piperazinyl]propanol
• 英文别名: [4-(3-trifluoromethylphenyl)piperazino]-propanol；3-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-propan-1-ol；3-{4-[3-(Trifluoromethyl)phenyl]piperazin-1-yl}propan-1-ol；3-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propan-1-ol
• CAS: 32212-47-8
• 化学式: C₁₄H₁₉F₃N₂O
• 分子量: 288.313
• InChiKey: UEZPJLWDYMUKQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-methyladamantane-1-acetic acid chloride 、 3-[4-(3-trifluoromethylphenyl)-1-piperazinyl]propanol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以38%的产率得到3-Methyltricyclo[3.3.1.13,7 ]decane-1-acetic acid 3-[4-[3-(trifluoromethyl)phenyl]-1-piperazinyl]propyl ester
  参考文献：
  名称：

  Adamantyl- and fluorenyl-arylpiperazines and -arylpiperidines

  摘要：

  化合物##STR1##中，其中R.sup.1是1-金刚烷基，3-甲基-1-金刚烷基，9-芴基或1-芴基；n为0或1；m为1、2、3、4或5；X为##STR2##其中R.sup.2是苯基，苄基，吡啶基，嘧啶基，吡嗪基或取代苯基或苄基，其中取代基是1到6个碳原子的烷基，1到6个碳原子的烷氧基，卤素，氰基，硝基或三氟甲基，##STR3##其中R.sup.3是氢，1到6个碳原子的烷基，1到6个碳原子的烷氧基，卤素，氰基或硝基；或其药学上可接受的盐是有用的抗抑郁和/或抗焦虑剂。

  公开号：

  US04797489A1
• 作为产物：
  描述：

  1-(3-三氟甲基苯基)哌嗪 、 3-氯-1-丙醇 、 potassium carbonate 以68%的产率得到
  参考文献：
  名称：

  FELFOELDI, K.;MOLNAR, A.;APJOK, J.;CZOMBOS, J.;NOTHEISZ, F.;KARPATI, E., ACTA PHYS. ET CHEM. SZEGED, 1982, 28, N 3-4, 225-244

  摘要：

  DOI：

文献信息

• Piperazinyl derivatives and methods of treating central nervous system
  申请人：Novo Nordisk A/S

  公开号：US05246935A1

  公开（公告）日：1993-09-21

  Piperazinyl derivatives of the general formula I ##STR1## wherein R.sup.1 represents substituted phenyl, 1- or 2-diazanaphthyl, azadiazanaphtyl or diazanaphtyl groups; n is 1, 2, 3 or 4; X is --O-- or ##STR2## wherein R.sup.2 is hydrogen, C.sub.1-6 -alkyl or C.sub.3-8 -cycloalkyl; Y is .dbd.O or .dbd.S or .dbd.NZ wherein Z is hydrogen, C.sub.1-6 -alkyl or --CN and R.sup.3 is selected from a group consisting of various structures have been found to exhibit high affinity for various receptor subtypes including the 5-HT.sub.2 receptor, the 5-HT.sub.1A receptor, the alpha.sub.1 receptor the dopamine receptor or a combination of these and may therefore be useful for treating CNS system, cardiovascular system and gastrointestinal disorders.

  通式I的吡哌啉衍生物 其中R.sup.1代表取代苯基，1-或2-二氮杂萘基，氮杂萘基或二氮杂萘基；n为1、2、3或4；X为--O--或 其中R.sup.2为氢、C.sub.1-6-烷基或C.sub.3-8-环烷基；Y为.dbd.O、.dbd.S或.dbd.NZ，其中Z为氢、C.sub.1-6-烷基或--CN，R.sup.3从一组中选择，该组包括各种结构已被发现对各种受体亚型表现出高亲和力，包括5-HT.sub.2受体，5-HT.sub.1A受体，alpha.sub.1受体，多巴胺受体或这些受体的组合，因此可能对治疗中枢神经系统，心血管系统和胃肠道疾病有用。
• Piperazinylalkoxyindanes and acid addition salts thereof
  申请人：MITSUBISHI KASEI CORPORATION

  公开号：EP0021368A1

  公开（公告）日：1981-01-07

  Piperazinylalkoxyindanes having the general formula wherein n is an integer of 3 or 4; R1 is hydrogen, halogen, alkyl, alkoxy, hydroxy, phenyl or nitro; and R2 is phenyl or pyridyl optionally having at least one substituent selected from the group consisting of halogen, trifluoromethyl, alkoxy and alkylcarbonyl, and acid addition salts thereof are disclosed, which have anti-anxiety activity and are effective as sedatives.

  通式如下的哌嗪基烷氧基茚满酮 其中 n 是 3 或 4 的整数；R1 是氢、卤素、烷基、烷氧基、羟基、苯基或硝基；R2 是苯基或吡啶基，可选择具有至少一个从卤素、三氟甲基、烷氧基和烷基羰基组成的组中选出的取代基，本发明公开了这些化合物及其酸加成盐，它们具有抗焦虑活性，可有效用作镇静剂。
• 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.
• PIPERAZINYL DERIVATIVES
  申请人：NOVO NORDISK A/S

  公开号：EP0544765A1

  公开（公告）日：1993-06-09
• US4140790A
  申请人：——

  公开号：US4140790A

  公开（公告）日：1979-02-20