1-(2-丁基-苯基)-哌嗪 | 100861-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-(2-丁基-苯基)-哌嗪
• 英文名称: 1-(2-butyl-phenyl)-piperazine
• 英文别名: 1-<2-Butyl-phenyl>-piperazin；1-(2-butylphenyl)piperazine
• CAS: 100861-48-1
• 化学式: C₁₄H₂₂N₂
• 分子量: 218.342
• InChiKey: XJZVCNGBKRTGFO-UHFFFAOYSA-N

物化性质

• 沸点：
  349.1±30.0 °C(Predicted)
• 密度：
  0.976±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 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：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-丁基-苯基)-哌嗪 、 N-(1,2,3,4-tetrahydronaphthalen-1-yl)-6-bromohexanamide 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以43%的产率得到6-[4-(2-butylphenyl)piperazin-1-yl]-N-(1,2,3,4-tetrahydronaphthalen-1-yl)hexanamide
  参考文献：
  名称：

  Structure−Activity Relationship Study on N-(1,2,3,4-Tetrahydronaphthalen-1-yl)-4-aryl-1-piperazinehexanamides, a Class of 5-HT₇ Receptor Agents. 2

  摘要：

  Here we report the synthesis of N-(1,2,3,4-tetrahydronaphthalen-1-yl)-4-aryl-1-piperazinealkylamides 16-29 that were designed to elucidate both structure-affinity and -activity relationships for the 5-HT7 receptor, by targeting the substituent in 2-position of the aryl linked to the piperazine ring. The affinities of 16-29 for 5-HT7, 5-HT1A, 5-HT2A, and D-2 receptors were assessed by radioligand binding assays. The intrinsic activities at the 5-HT7 receptor of the most potent compounds were determined. A series of substituents covering a wide range of electronic, steric, and polar properties was evaluated, revealing a key role on 5-HT7 receptor affinity and intrinsic activity. Certain lipophilic substituents (SCH3, CH(CH3)(2), N(CH3)(2), CH3, Ph) led to high-affinity agonists, whereas OH and NHCH3 substituents switched intrinsic activity toward antagonism. 4-[2-(1-Methylethyl)phenyl]-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1-piperazinehexanamide (19), 4-(2-diphenyl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1-piperazinehexanamide (21), and 4-(2-dimethylaminophenyl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1-piperazinehexanamide (22) were identified as potent 5-HT7 receptor agonists (K-i = 0.13-1.1 nM, EC50 = 0.90-1.77 mu M), showing selectivity over 5-HT1A, 5-HT2A, and D-2 receptors.

  DOI：

  10.1021/jm070487n
• 作为产物：
  描述：

  二(2-氯乙基)胺盐酸盐 、 2-丁基苯胺 在 sodium carbonate 作用下， 生成 1-(2-丁基-苯基)-哌嗪
  参考文献：
  名称：

  Activity of aromatic substituted phenylpiperazines lacking affinity for dopamine binding sites in a preclinical test of antipsychotic efficacy

  摘要：

  Generally, antipsychotic agents are dopamine receptor blocking agents that also block conditioned avoidance responding (CAR) in the rat. Recently, however, both (Q-methoxyphenyl)piperazine (OMPP, 1h) and (m-chlorophenyl)piperazine (MCPP, 1o) have been reported to block conditioned avoidance responding in the rat although neither has dopamine receptor blocking properties. The present paper examines the behavioral and biochemical profile of a number of additional substituted phenylpiperazines. None of the phenylpiperazines tested demonstrated high affinity for either dopamine D-1 or D-2 receptor sites, yet many were effective in blocking CAR. The results suggest that the phenylpiperazines may be effective antipsychotic agents without blocking dopamine receptors. Moreover, the active compounds did demonstrate activity in displacing ligand binding to serotonin receptors. Receptor binding profiles were determined for 5-HT-1A and 5-HT-1B binding sites as well as for 5-HT-2 sites. The data from this preclinical test suggest these phenylpiperazines might be effective antipsychotic agents acting via a nondopaminergic mechanism of action.

  DOI：

  10.1021/jm00125a020

文献信息

• Pyrrole Mannich bases as potential antipsychotic agents
  作者：Malcolm K. Scott、Gregory E. Martin、Deena L. DiStefano、Cynthia L. Fedde、Michael J. Kukla、Donna L. Barrett、William J. Baldy、Robert J. Elgin、James M. Kesslick

  DOI：10.1021/jm00081a018

  日期：1992.2

  receptors, they are reasonably potent in inhibiting conditioned avoidance responding (CAR) in the rat, an indication of potential antipsychotic activity. Conversion of these arylpiperazines to pyrrole Mannich bases has provided a series of compounds (10-44) which exhibit potent inhibition of CAR when given po and have strong affinity for both the D-2 and 5-HT-1A binding sites. Some of these agents also

  最近，我们报道了一系列芳基哌嗪4，它们对5-羟色胺5-HT-1A和5-HT-1B结合位点表现出高亲和力。尽管这些化合物与多巴胺D-1和D-2受体的相互作用较弱，但它们在抑制大鼠的条件回避反应（CAR）方面具有相当强的效力，这是潜在抗精神病药活性的指标。这些芳基哌嗪向吡咯曼尼希碱的转化提供了一系列化合物（10-44），当给予po时，它们显示出对CAR的有效抑制，并且对D-2和5-HT-1A结合位点都具有强亲和力。这些试剂中的一些也不能产生僵直症。
• PIPERAZINE DERIVATIVES AND PROCESS FOR THE PREPARATION THEREOF
  申请人：Samjin Pharmaceutical Co., Ltd.

  公开号：EP1075469A1

  公开（公告）日：2001-02-14
• THERAPEUTICALLY ACTIVE COMPOUNDS FOR USE IN THE TREATMENT OF CANCER CHARACTERIZED AS HAVING AN IDH MUTATION
  申请人：Agios Pharmaceuticals, Inc.

  公开号：EP2509600B1

  公开（公告）日：2017-08-02
• US7235538B2
  申请人：——

  公开号：US7235538B2

  公开（公告）日：2007-06-26
• [EN] PIPERAZINE DERIVATIVES AND PROCESS FOR THE PREPARATION THEREOF<br/>[FR] DERIVES DE PIPERAZINE ET LEUR PROCEDE DE PREPARATION
  申请人：SAMJIN PHARM CO LTD

  公开号：WO2000052001A1

  公开（公告）日：2000-09-08

  The present invention relates to a novel compound of general formula (I) and its pharmaceutically acceptable acid addition salt, and process for the preparation thereof, which have strong antitumor activities and very low toxicity, wherein R1 and R2 are independently hydrogen, C1-C4 alkyl, C1-C4 alkylcarboxyl, C1-C4 alkylcarbonyl, C1-C4 alkoxy, C1-C4 hydroxyalkyl, C1-C4 aminoalkyl or C1-C4 hydroxyiminoalkyl, or R1 and R2 are fused to form C3-C4 unsaturated ring; R3, R4, R5, R6 and R7 are independently hydrogen, halogen, hydroxy, nitro, amino, C1-C4 alkyl, C1-C4 alkylcarboxyl, C1-C4 alkylcarbonyl, C1-C4 alkoxy or C1-C4 thioalkoxy; R8 is C1-C4 alkyl; Y is oxygen, sulphur, amino, substituted amino or C1-C4 thioalkyl; Z is C1-C4 alkoxy, C1-C4 alkyl, C1-C4 alkylamino or C1-C4 thioalkoxy; X1 and X2 are independently carbon or nitrogen; and -N--C- and -C--Y- may form a single bond or a double bond provided that if -N--C- forms a single bond, -C--Y- forms a double bond, and if -C--Y- forms a single bond, -N--C- forms a double bond and R8 is nonexistent.