3-(6-(piperidin-1-yl)-9H-purin-2-yl)phenol | 1062204-19-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 3-(6-(piperidin-1-yl)-9H-purin-2-yl)phenol
• 英文别名: 3-(6-piperidin-1-yl-7H-purin-2-yl)phenol
• CAS: 1062204-19-6
• 化学式: C₁₆H₁₇N₅O
• 分子量: 295.344
• InChiKey: HBKAYDPFQWXZQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  77.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-amino-4-(piperidinylamidino)imidazole 、 间羟基苯甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 以63%的产率得到3-(6-(piperidin-1-yl)-9H-purin-2-yl)phenol
  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

• IMIDAZOLOPYRIMIDINE ANALOGS AND THEIR USE AS PI3 KINASE AND MTOR INHIBITORS
  申请人：Bursavich Matthew Gregory

  公开号：US20080233127A1

  公开（公告）日：2008-09-25

  The present invention relates to Imidazolopyrimidine Analogs, methods of making Imidazolopyrimidine Analogs, compositions comprising an Imidazolopyrimidine Analog, and methods for treating or preventing a PI3K-related disorder comprising administering to a subject in need thereof an effective amount of an Imidazolopyrimidine Analog. The invention also relates to methods for treating or preventing mTOR-related disorders comprising administering to a subject in need thereof an effective amount of an Imidazolopyrimidine Analog.

  本发明涉及咪唑吡嘧啶类似物，制备咪唑吡嘧啶类似物的方法，包含咪唑吡嘧啶类似物的组合物，以及治疗或预防PI3K相关疾病的方法，包括向需要的受试者施用有效量的咪唑吡嘧啶类似物。该发明还涉及治疗或预防mTOR相关疾病的方法，包括向需要的受试者施用有效量的咪唑吡嘧啶类似物。
• Novel purine and pyrazolo[3,4-d]pyrimidine inhibitors of PI3 kinase-α: Hit to lead studies
  作者：Adam M. Gilbert、Pawel Nowak、Natasja Brooijmans、Matthew G. Bursavich、Christoph Dehnhardt、Efren Delos Santos、Larry R. Feldberg、Irwin Hollander、Stephen Kim、Sabrina Lombardi、Kaapjoo Park、Aranapakam M. Venkatesan、Robert Mallon

  DOI：10.1016/j.bmcl.2009.11.051

  日期：2010.1

  Series of purine and pyrazolo[3,4-d] pyrimidine inhibitors of phosphatidylinositol-3-kinases (PI3K) have been prepared. The optimized purine inhibitors show good potency in a PI3K p110 alpha (PI3K-alpha) fluorescence polarization assay with good selectivity versus PI3K p110 gamma (PI3K-gamma) and the mammalian target of rapamycin (mTOR). The related pyrazolo[3,4-d]pyrimidines show potent PI3K-alpha and mTOR inhibition with good selectivity versus PI3K-gamma. Representative compounds showed activity in a cellular proliferation assay against Caco-2 colorectal, LoVo colorectal and PC3MM2 prostate adenocarcinoma cancer cells. Signaling through the PI3K pathway was confirmed via inhibition of phospho-AKT in MDA-361 cells. (C) 2009 Elsevier Ltd. All rights reserved.
• [EN] IMIDAZOLOPYRIMIDINE ANALOGS AND THEIR USE AS PI3 KINASE AND MTOR INHIBITORS<br/>[FR] ANALOGUES D'IMIDAZOLOPYRIMIDINE ET LEUR UTILISATION COMME INHIBITEURS DE PI3 KINASE ET DE MTOR
  申请人：WYETH CORP

  公开号：WO2008116129A2

  公开（公告）日：2008-09-25

  [EN] The present invention relates to Imidazolopyrimidine Analogs, methods of making Imidazolopyrimidine Analogs, compositions comprising an Imidazolopyrimidine Analog, and methods for treating or preventing a PI3K-related disorder comprising administering to a subject in need thereof an effective amount of an Imidazolopyrimidine Analog. The invention also relates to methods for treating or preventing mTOR -related disorders comprising administering to a subject in need thereof an effective amount of an Imidazolopyrimidine Analog.
  [FR] La présente invention concerne des angalogues d'imidazolopyrimidine, des procédés de préparation d'analogues d'imidazolopyrimidine, des compositions comprenant un analogue d'imidazolopyrimidine, et des procédés de traitement ou de prévention d'un trouble lié au PI3K comprenant l'administration à un sujet qui en a besoin d'une quantité efficace d'un analogue d'imidazolopyrimidine. L'invention concerne également un procédé de traitement ou de prévention de troubles liés au MTOR comprenant l'administration à un sujet qui en a besoin d'une quantité efficace d'analogue d'imidazolopyrimidine.
• 2-Aryladenine derivatives as a potent scaffold for A1, A3 and dual A1/A3 adenosine receptor antagonists: Synthesis and structure-activity relationships
  作者：Filipe Areias、Carla Correia、Ashly Rocha、José Brea、Marián Castro、Maria I. Loza、M. Fernanda Proença、M. Alice Carvalho

  DOI：10.1016/j.bmc.2019.06.034

  日期：2019.8

  human A1 adenosine receptor containing a new purine scaffold. To study the structure activity relationships of this new chemical series for adenosine receptors, a library of 24 purines was synthesized and tested in radioligand binding assays at human A1, A2A, A2B and A3 adenosine receptor subtypes. Fourteen molecules showed potent antagonism at A1, A3 or dual A1/A3 adenosine receptors. This purine scaffold

  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。