2-(2-(4-(pyrimidin-2-yl)piperazin-1-yl)ethyl)isoindoline-1,3-dione | 95847-91-9

• 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-(2-(4-(pyrimidin-2-yl)piperazin-1-yl)ethyl)isoindoline-1,3-dione
• 英文别名: N-{2-[4-(2-pyrimidinyl)-1-piperazinyl]ethyl}phthalimide；2-{2-[4-(pyrimidin-2-yl)piperazin-1-yl]ethyl}-1H-isoindole-1,3(2H)-dione；2-[2-(4-pyrimidin-2-ylpiperazin-1-yl)ethyl]isoindole-1,3-dione
• CAS: 95847-91-9
• 化学式: C₁₈H₁₉N₅O₂
• mdl: MFCD11044075
• 分子量: 337.381
• InChiKey: SJFQBFYOIPUMAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-(4-(pyrimidin-2-yl)piperazin-1-yl)ethyl)isoindoline-1,3-dione 在 肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-(4-(嘧啶-2-基)哌嗪-1-基)乙胺
  参考文献：
  名称：

  Synthesis and biological evaluation of novel T-type Ca2+ channel blockers

  摘要：

  A small molecule library of piperazinylalkylisoxazole derivatives containing about 600 compounds was designed, synthesized and evaluated for blocking effects on T-type Ca2+ channel. Several ligands were identified to possess high inhibitory activity against the T-type Ca2+ channel. The compound 21 with trifluoromethyl substituents at C-3-position of phenyl group (W) and C-2-position of phenyl group (R-2) showed the highest inhibitory activity with IC50 value of 1.02 muM, which is comparable to that of mibefradil. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.011
• 作为产物：
  描述：

  三乙烯二胺 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 生成 2-(2-(4-(pyrimidin-2-yl)piperazin-1-yl)ethyl)isoindoline-1,3-dione
  参考文献：
  名称：

  微波辐射条件下有效的一锅两步合成4-取代的1-杂芳基哌嗪

  摘要：

  已经开发出一种高效的一锅两步微波程序，用于合成4-取代的1-杂芳基哌嗪。将杂芳基氯化物与1,4-二氮杂双环[2.2.2]辛烷（DABCO）在160°C微波加热15分钟，得到1-杂芳基-4-（2-氯乙基）哌嗪，可以进一步与各种亲核试剂反应，再次在微波辐射条件下，以良好至优异的产率得到4-取代的1-杂芳基哌嗪阵列。

  DOI：

  10.1016/j.tetlet.2007.02.114

文献信息

• Novel Synthesis of Heterocycle-Containing Adamantane Derivatives
  作者：Xiaojian Xu、Jianwei Guo、Qiang Su、Xing Zhong

  DOI：10.14233/ajchem.2013.15214

  日期：——

  A novel approach to synthesize the of heterocycle-containing adamantane derivatives 1-[(3-hydroxy-1-adamantyl)amino]acetyl}-2-cyano-(S)-pyrrolidine and N-2-[4-(2-pyrimidinyl)-1-piperazinyl]ethyl}adamantane-1-carboxamide, which were effective in treatment of diabetes and depression respectively, have been described. The target compounds were synthesized by raw materials of inexpensive L-proline and available 1-(2-pyrimidinyl) piperazine respectively. Compared with traditional synthetic routes, the method provides several advantages such as inexpensive and readily available raw materials, convenient manipulation and high yield.

  一种合成含杂环金刚烷衍生物的新方法已经描述，该方法合成了1-[(3-羟基-1-金刚烷基)氨基]乙酰基}-2-氰基-(S)-吡咯烷和N-2-[4-(2-嘧啶基)-1-哌嗪基]乙基}金刚烷-1-羧酰胺，两种衍生物分别对糖尿病和抑郁症治疗有效。目标化合物分别以廉价的L-脯氨酸和可供应的1-(2-嘧啶基)哌嗪为原材料合成。与传统合成路线相比，该方法具有多个优点，如原材料价格低廉且易获取、操作简便和高产率。
• Facile N-Alkylation/N′-Arylation Process: A Direct Approach to Aromatic Aminoalkyl Amines
  作者：Qiming Zhu、Mingwei Chen、Jinyu Hu、Luyi Yang

  DOI：10.1002/asia.201800193

  日期：2018.5.4

  N‐alkylation/N′‐arylation process in a multicomponent reaction with secondary amines, cyclic tertiary amines and electron‐deficient aryl halides has been described. In this case, the N‐alkylation of secondary amines, utilizing cyclic tertiary amines as alkyl group sources, is enabled by a facile C−N cleavage. Such an operationally simple method could facilitate access to aromatic aminoalkyl amines,

  描述了一个有趣的CN转换，涉及与仲胺，环状叔胺和缺电子的芳基卤化物发生多组分反应的无催化剂的N-烷基化/ N'-芳基化过程。在这种情况下，通过环状叔胺的轻松裂解，可以将环状叔胺用作烷基源，实现仲胺的N-烷基化。这种操作简单的方法可以方便地获得芳香族氨基烷基胺（含氮生物活性分子），收率很好。
• 2-Pyrimidinyl-l-piperazin-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
  申请人：Troponwerke GmbH & Co. KG

  公开号：EP0129128A2

  公开（公告）日：1984-12-27

  Die vorliegende Erfindung betrifft neue substituierte 2-Pyrimidinyt-l-piperazin.Denvate der allgemeinen Formel (I), Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel, insbesondere das zentrale Nervensystem beeinflussende Mittel.

  本发明涉及通式（I）的新取代的 2-嘧啶基-l-哌嗪变性物、其制备工艺和含有它们的药物，特别是影响中枢神经系统的药物。
• 10.3390/molecules29153528
  作者：Krzyżak, Edward、Marciniak, Aleksandra、Szkatuła, Dominika、Jankowska, Klaudia A.、Dobies, Natalia、Kotynia, Aleksandra

  DOI：10.3390/molecules29153528

  日期：——

  NMR, FT-IR, and ESI–MS techniques. For all imides, the inhibitory activity against AChE and BuChE was tested using Ellaman’s method. IC50 values were determined. The best results were obtained for the derivative I, with a phenyl substituent at position 4 of piperazine, IC50 = 1.12mM (AChE) and for the derivative III, with a diphenylmethyl moiety, with IC50 = 21.24 μM (BuChE). The compounds tested in

  1,3-异吲哚啉二酮衍生物因其生物活性而备受关注，例如抗炎和抗菌作用。已经针对阿尔茨海默氏症候选疗法设计并评估了几个系列。他们表现出了有希望的活动。在这项工作中，首先在计算机研究中测试了六种新衍生物对乙酰胆碱酯酶 (AChE) 和丁酰胆碱酯酶 (BuChE) 的抑制能力。应用分子对接和分子动力学模拟。接下来，合成这些化合物并通过 1H NMR、13C NMR、FT-IR 和 ESI-MS 技术进行表征。对于所有酰亚胺，使用 Ellaman 方法测试了对 AChE 和 BuChE 的抑制活性。测定IC50值。哌嗪 4 位有苯基取代基的衍生物 I 获得了最佳结果，IC50 = 1.12 mM (AChE)；具有二苯甲基部分的衍生物 III 的 IC50 = 21.24 μM (BuChE)。这项工作中测试的化合物为进一步的结构修饰提供了坚实的基础，从而有效设计了两种胆碱酯酶的潜在抑制剂。
• Synthesis and biological evaluation of novel T-type Ca2+ channel blockers
  作者：Hee Kyung Jung、Munikumar Reddy Doddareddy、Joo Hwan Cha、Hyewhon Rhim、Yong Seo Cho、Hun Yeong Koh、Bong Young Jung、Ae Nim Pae

  DOI：10.1016/j.bmc.2004.06.011

  日期：2004.8.1

  A small molecule library of piperazinylalkylisoxazole derivatives containing about 600 compounds was designed, synthesized and evaluated for blocking effects on T-type Ca2+ channel. Several ligands were identified to possess high inhibitory activity against the T-type Ca2+ channel. The compound 21 with trifluoromethyl substituents at C-3-position of phenyl group (W) and C-2-position of phenyl group (R-2) showed the highest inhibitory activity with IC50 value of 1.02 muM, which is comparable to that of mibefradil. (C) 2004 Elsevier Ltd. All rights reserved.