2-[3-[4-(o-tolyl)piperazin-1-yl]propyl]isoindoline-1,3-dione | 102391-89-9

• 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: 2-[3-[4-(o-tolyl)piperazin-1-yl]propyl]isoindoline-1,3-dione
• 英文别名: N-[3-(4-o-tolyl-piperazin-1-yl)-propyl]-phthalimide；N-[3-[4-(2-methylphenyl)-1-piperazinyl]propyl]phthalimide；2-[3-[4-(2-methylphenyl)piperazin-1-yl]propyl]isoindole-1,3-dione
• CAS: 102391-89-9
• 化学式: C₂₂H₂₅N₃O₂
• 分子量: 363.459
• InChiKey: ZMVRPKIJGHYKCS-UHFFFAOYSA-N

物化性质

• 沸点：
  531.2±50.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[3-[4-(o-tolyl)piperazin-1-yl]propyl]isoindoline-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 3-[4-(o-tolyl)piperazin-1-yl]propan-1-amine
  参考文献：
  名称：

  Synthesis and biological evaluation of oxazole derivatives as T-type calcium channel blockers

  摘要：

  T-type calcium channel is one of therapeutic targets for the treatment of cardiovascular diseases and neuropathic pain. In this study, as a part of our ongoing efforts to develop potent T-type calcium channel blockers, we designed oxazole derivatives substituted with arylpiperazinylalkylamines. The oxazoles were synthesized in a convenient convergent synthetic method, and biologically evaluated against alpha(1G) (Ca(V)3.1) T-type calcium channel. Among total 41 oxazole compounds synthesized, the most active one was the compound 10-35 with an IC(50) value of 0.65 mu M, which is comparable with that of mibefradil. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.030
• 作为产物：
  描述：

  1-(2-甲基苯基)哌嗪 、 N-(3-溴丙基)苯二胺 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 2-[3-[4-(o-tolyl)piperazin-1-yl]propyl]isoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of oxazole derivatives as T-type calcium channel blockers

  摘要：

  T-type calcium channel is one of therapeutic targets for the treatment of cardiovascular diseases and neuropathic pain. In this study, as a part of our ongoing efforts to develop potent T-type calcium channel blockers, we designed oxazole derivatives substituted with arylpiperazinylalkylamines. The oxazoles were synthesized in a convenient convergent synthetic method, and biologically evaluated against alpha(1G) (Ca(V)3.1) T-type calcium channel. Among total 41 oxazole compounds synthesized, the most active one was the compound 10-35 with an IC(50) value of 0.65 mu M, which is comparable with that of mibefradil. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.030

文献信息

• [EN] PHENYL CARBAMATES AND THEIR USE AS INHIBITORS OF THE FATTY ACID AMIDE HYDROLASE (FAAH) ENZYME AND MODULATORS OF THE D3 DOPAMINE RECEPTOR (D3DR)<br/>[FR] PHENYL CARBAMATES ET LEUR UTILISATION COMME INHIBITEURS DE L'ENZYME HYDROLASE D'AMIDES D'ACIDES GRAS (FAAH) ET MODULATEURS DU RÉCEPTEUR D3 DE LA DOPAMINE (D3DR)
  申请人：FOND ISTITUTO ITALIANO DI TECNOLOGIA

  公开号：WO2015007615A1

  公开（公告）日：2015-01-22

  The invention provides compounds of Formula (I) or pharmaceutically acceptable salts thereof wherein Ar', R1, R2, R3, R4, X, Y are as defined in the description of invention, as multi-target directed ligands (MTDLs) that are at the same time inhibitors of the fatty acid amide hydrolase (FAAH) enzyme and modulators of the D3 dopamine receptor (D3DR), their methods of preparation, formulations and therapeutic applications thereof.

  该发明提供了式（I）的化合物或其药用可接受的盐，其中Ar'，R1，R2，R3，R4，X，Y如发明描述中所定义，作为多靶点定向配体（MTDLs），同时是脂肪酸酰胺水解酶（FAAH）酶的抑制剂和D3多巴胺受体（D3DR）的调节剂，以及它们的制备方法、配方和治疗应用。
• PHENYL CARBAMATES AND THEIR USE AS INHIBITORS OF THE FATTY ACID AMIDE HYDROLASE (FAAH) ENZYME AND MODULATORS OF THE D3 DOPAMINE RECEPTOR (D3DR)
  申请人：FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA

  公开号：US20160194296A1

  公开（公告）日：2016-07-07

  The invention provides compounds of Formula (I) or pharmaceutically acceptable salts thereof wherein Ar′, R 1 , R 2 , R 3 , R 4 , X, Y are as defined in the description of invention, as multi-target directed ligands (MTDLs) that are at the same time inhibitors of the fatty acid amide hydrolase (FAAH) enzyme and modulators of the D3 dopamine receptor (D3DR), their methods of preparation, formulations and therapeutic applications thereof.

  本发明提供了化合物I或其药学上可接受的盐，其中Ar′、R1、R2、R3、R4、X、Y的定义如本发明描述中所述，作为多靶点定向配体（MTDLs），同时作为脂肪酸酰胺水解酶（FAAH）酶的抑制剂和D3多巴胺受体（D3DR）的调节剂，以及它们的制备方法、配方和治疗应用。
• <i>N-</i>Arylpiperazinyl-<i>N</i>‘<i>-</i>propylamino Derivatives of Heteroaryl Amides as Functional Uroselective α₁-Adrenoceptor Antagonists
  作者：Todd R. Elworthy、Anthony P. D. W. Ford、Gary W. Bantle、David J. Morgans,、Rachel S. Ozer、Wylie S. Palmer、David B. Repke、Magarita Romero、Leticia Sandoval、Eric B. Sjogren、Francisco X. Talamás、Alfredo Vazquez、Helen Wu、Nicolas F. Arredondo、David R. Blue,、Andrea DeSousa、Lisa M. Gross、M. Shannon Kava、John D. Lesnick、Rachel L. Vimont、Timothy J. Williams、Quan-Ming Zhu、Jürg R. Pfister、David E. Clarke

  DOI：10.1021/jm970166j

  日期：1997.8.1

  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.
• US4585773A
  申请人：——

  公开号：US4585773A

  公开（公告）日：1986-04-29
• US9828352B2
  申请人：——

  公开号：US9828352B2

  公开（公告）日：2017-11-28