1-(2-丙基苯基)哌嗪 | 119695-81-7

• 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-丙基苯基)哌嗪
• 英文名称: 1-(2-propylphenyl)piperazine
• 英文别名: Piperazine, 1-(2-propylphenyl)-
• CAS: 119695-81-7
• 化学式: C₁₃H₂₀N₂
• 分子量: 204.315
• InChiKey: FHIDPEUFJOUCRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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-丙基苯基)哌嗪 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 29.0h， 生成 N,N-Dimethyl-2-{3-[4-(2-propyl-phenyl)-piperazin-1-yl]-propylamino}-nicotinamide
  参考文献：
  名称：

  N-Arylpiperazinyl-N‘-propylamino Derivatives of Heteroaryl Amides as Functional Uroselective α₁-Adrenoceptor Antagonists

  摘要：

  Novel arylpiperazines were identified as alpha(1)-adrenoceptor(BR) subtype-selective antagonists by functional in vitro screening. 3-[4-(ortho-Substituted phenyl)piperazin-1-yl]propylamines were derivatized with N,N-dimethyl anthranilamides, nicotinamides,;as well as carboxamides of quinoline, I,8-naphthyridine, pyrazolo[3,4-b]pyridine, isoxazolo[3,4-b]pyridine, imidazo[4,5-b]pyridine, and pyrazolo[1,5-a]pyrimidines. Strips of rabbit bladder neck were employed as a predictive assay for antagonism in the human lower tract. Rings of rat aorta;a were used as a ''negative screen'' for the test antagonists. Binding to alpha(1)-ARs was relatively sensitive to size and electronic features of the arylpiperazine portion of the antagonists and permissive to these features on the heteroaryl carboxamide side. These structure-affinity findings were exploited to produce nicotinamides (e.g, 13ii and 25x) and pyrazolo[3,4-b]pyridines (e.g. 37f and 37y) ligands with nanomolar affinity at the alpha(1)-AR subtype prevalent in the human lower urinary tract (pA(2) values: 8.8, 10.7, 9.3, and 9.9, respectively) and displaying 2-3 orders of magnitude selectivity over the alpha(1D)-AR.

  DOI：

  10.1021/jm970166j
• 作为产物：
  描述：

  二(2-氯乙基)胺盐酸盐 、 2-丙基苯胺 在 sodium carbonate 作用下， 生成 1-(2-丙基苯基)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。
• [EN] NICOTINIC RECEPTOR AGONISTS FOR THE TREATMENT OF INFLAMMATORY DISEASES<br/>[FR] AGONISTES DU RECEPTEUR DE NICOTINE POUR LE TRAITEMENT DE MALADIES INFLAMMATOIRES
  申请人：UNIV LAVAL

  公开号：WO2006005195A1

  公开（公告）日：2006-01-19

  This invention relates to the use of nicotine receptor agonists or analogs or derivatives thereof for treating inflammatory pulmonary diseases. The invention further relates to pharmaceutical compositions comprising nicotine receptor agonists or analogs or derivatives thereof. Novel compounds of formula wherein R1 ,R2 ,Xa and Ya are as defined herein are also provided.

  本发明涉及使用尼古丁受体激动剂或类似物或其衍生物治疗炎症性肺部疾病。本发明还涉及包含尼古丁受体激动剂或类似物或其衍生物的制药组合物。还提供了公式中R1，R2，Xa和Ya如定义所述的新化合物。
• [EN] NOVEL 4-ARYLPIPERAZINES AND 4-ARYLPIPERIDINES
  申请人：McNEILAB, INC.

  公开号：WO1993004684A1

  公开（公告）日：1993-03-18

  (EN) Compounds of the general formula (I) are disclosed as novel antipsychotic agents.(FR) Cette invention concerne des composés de formule (I) utiles comme nouveaux agents antipsychotiques.

  (I)式化合物被披露为新型抗精神病药物。(FR)该发明涉及公式（I）的化合物，作为新型抗精神病药物。
• Nicotinic Receptor Agonists for the Treatment of Inflammatory Diseases
  申请人：Cormier Yvon

  公开号：US20080221085A1

  公开（公告）日：2008-09-11

  Nicotine receptor agonists or analogs or derivatives thereof for treating inflammatory pulmonary diseases, and pharmaceutical compositions including nicotine receptor agonists or analogs or derivatives thereof. Compounds of formula wherein R1, R2, Xa and Ya are as defined herein are also provided.

  尼古丁受体激动剂或类似物或其衍生物用于治疗炎症性肺部疾病，以及包括尼古丁受体激动剂或类似物或其衍生物的制药组合物。本文还提供了式中R1、R2、Xa和Ya所定义的化合物。
• NICOTINIC RECEPTOR AGONISTS FOR THE TREATMENT OF INFLAMMATORY DISEASES
  申请人：CORMIER YVON

  公开号：US20120022049A1

  公开（公告）日：2012-01-26

  Nicotine receptor agonists or analogs or derivatives thereof for treating inflammatory pulmonary diseases, and pharmaceutical compositions including nicotine receptor agonists or analogs or derivatives thereof. Compounds of formula wherein R1, R2, Xa and Ya are as defined herein are also provided.

  尼古丁受体激动剂、类似物或其衍生物用于治疗炎症性肺部疾病，以及包含尼古丁受体激动剂、类似物或其衍生物的制药组合物。此外，还提供了公式中R1、R2、Xa和Ya定义如下的化合物。