6-(4-methylpiperazin-1-yl)-9H-purine | 99172-01-7

• 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: 6-(4-methylpiperazin-1-yl)-9H-purine
• 英文别名: 6-(4-methylpiperazin-1-yl)-7H-purine
• CAS: 99172-01-7
• 化学式: C₁₀H₁₄N₆
• mdl: MFCD01808743
• 分子量: 218.261
• InChiKey: AXPCNBLIEMWMMG-UHFFFAOYSA-N

物化性质

• 熔点：
  270 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  328.3±52.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)
• 溶解度：
  28.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(4-methylpiperazin-1-yl)-9H-purine 、 溴甲苯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以10%的产率得到9-benzyl-6-(4-methylpiperazin-1-yl)-9H-purine
  参考文献：
  名称：

  2,4-Diaminopyrimidines as histamine H4 receptor ligands—Scaffold optimization and pharmacological characterization

  摘要：

  The human histamine H-4 receptor (hH(4)R) is a promising new target in the therapy of inflammatory diseases and disorders of the immune system. For the development of new H4R antagonists a broad ligand-based virtual screening was performed resulting in two hits. The dissection of their common annelated aromatic core into its heteromonocyclic components showed that 2,4-diaminopyrimidine is a potent hH(4)R affinity scaffold, which was comprehensively investigated. Structure-activity relationship studies revealed that slight structural changes evoke extensive differences in functional activities and potencies: while o-and p-substituted benzyl amines mainly showed partial agonism, m-substituted and rigidified ones exhibited inverse agonist efficacy. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.059
• 作为产物：
  描述：

  N-甲基哌嗪 在 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 6-(4-methylpiperazin-1-yl)-9H-purine
  参考文献：
  名称：

  2-Aryladenine衍生物作为A1，A3和双重A1 / A3腺苷受体拮抗剂的有效支架：合成与构效关系。

  摘要：

  从包含1500多种学术化合物的馆藏中，通过计算机筛选筛选发现了含有新嘌呤支架的人A1腺苷受体的命中。为了研究该新化学系列腺苷受体的结构活性关系，合成了一个24个嘌呤的文库，并在人类A1，A2A，A2B和A3腺苷受体亚型的放射性配体结合测定中进行了测试。14个分子对A1，A3或双重A1 / A3腺苷受体表现出强烈的拮抗作用。嘌呤支架是新型生化工具和/或治疗药物的重要来源。

  DOI：

  10.1016/j.bmc.2019.06.034

文献信息

• Design and synthesis of purine analogues as highly specific ligands for FcyB, a ubiquitous fungal nucleobase transporter
  作者：Nikolaos Lougiakis、Efthymios-Spyridon Gavriil、Markelos Kairis、Georgia Sioupouli、George Lambrinidis、Dimitra Benaki、Emilia Krypotou、Emmanuel Mikros、Panagiotis Marakos、Nicole Pouli、George Diallinas

  DOI：10.1016/j.bmc.2016.09.055

  日期：2016.11

  In the course of our study on fungal purine transporters, a number of new 3-deazapurine analogues have been rationally designed, based on the interaction of purine substrates with the Aspergillus nidulans FcyB carrier, and synthesized following an effective synthetic procedure. Certain derivatives have been found to specifically inhibit FcyB-mediated [3H]-adenine uptake. Molecular simulations have

  在我们对真菌嘌呤转运蛋白的研究过程中，基于嘌呤底物与构巢曲霉FcγB载体的相互作用，合理地设计了许多新的3-脱氮嘌呤类似物，并按照有效的合成程序进行了合成。已经发现某些衍生物特异性抑制FcγB介导的[ 3 H]-腺嘌呤摄取。已经进行了分子模拟，表明所有活性化合物都通过与Asn163形成氢键与FcyB相互作用，而在3- deazaadenine的9和N 6位插入疏水片段增强了抑制作用。
• NOVEL COMPOUNDS AS MODULATORS OF PROTEIN KINASES
  申请人：NAGARATHNAM Dhanapalan

  公开号：US20120289496A1

  公开（公告）日：2012-11-15

  The present invention provides PI3K protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of kinase mediated diseases or disorders with them.

  本发明提供了PI3K蛋白激酶调节剂，其制备方法，含有它们的药物组合物，以及使用它们进行治疗、预防和/或改善激酶介导的疾病或紊乱的方法。
• Compounds as modulators of protein kinases
  申请人：Rhizen Pharmaceuticals SA

  公开号：US10220035B2

  公开（公告）日：2019-03-05

  The present invention provides PI3K protein kinase modulators, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of kinase mediated diseases or disorders with them.

  本发明提供了 PI3K 蛋白激酶调节剂、制备方法、含有这些调节剂的药物组合物以及用它们治疗、预防和/或改善激酶介导的疾病或紊乱的方法。
• Substituted chromenones as modulators of protein kinases
  申请人：Rhizen Pharmaceuticals SA

  公开号：US10322130B2

  公开（公告）日：2019-06-18

  The present invention provides PI3K protein kinase modulators of formula wherein R, Cy1, R1, R2, L1 and Cy2 are as defined herein. The present invention also relates to methods of preparing compounds of formula (I) to pharmaceutical compositions containing them and to methods of treatment, prevention and/or amelioration of kinase mediated diseases or disorders with them.

  本发明提供式 PI3K 蛋白激酶调节剂，其中 R、Cy1、R1、R2、L1 和 Cy2 如本文所定义。 本发明还涉及制备式（I）化合物的方法、含有式（I）化合物的药物组合物以及用式（I）化合物治疗、预防和/或改善激酶介导的疾病或紊乱的方法。
• Intermediates useful in the synthesis of compounds as modulators of protein kinases
  申请人：Rhizen Pharmaceuticals SA

  公开号：US11020399B2

  公开（公告）日：2021-06-01

  The present invention provides compounds of formula (10), formula (12), formula (14) and formula (15) wherein R, R1, R2, Cy1 and X are as described herein.

  本发明提供了式(10)、式(12)、式(14)和式(15)化合物 其中 R、R1、R2、Cy1 和 X 如本文所述。