2,6-二氯嘌呤盐酸盐 | 1073366-16-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2,6-二氯嘌呤盐酸盐
• 英文名称: 2,6-dichloropurin-9-ium chloride
• 英文别名: 2,6-dichloropurine hydrochloride；2,6-dichloro-7H-purine;hydrochloride
• CAS: 1073366-16-1
• 化学式: C₅H₂Cl₂N₄*ClH
• 分子量: 225.465
• InChiKey: XHQBZYJMMYUCCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙醇 、 2,6-二氯嘌呤盐酸盐 在 aluminum oxide 作用下， 反应 6.0h， 以55%的产率得到2-chloro-6-hydroxy-N-9-n-propyl-9H-purine
  参考文献：
  名称：

  N-Alkylation of 2,6-Dichloropurine Hydrochloride with a Variety of Alcohols over Alumina Catalyst

  摘要：

  2,6-Dichloropurine hydrochloride reacts with various types of alcohols using different alumina catalysts and converts into its N-9-alkyl-2-chloro-6-hydroxy-9H-purine products to an extent of 49-74%. The product selectivity depends on the stability of carbocation generated from the alcohol. More stable carbocation formulates both N-7 and N-9-alkyl-2,6-dichloropurine products, whereas the less stable carbocation results in exclusively N-9-alkyl-2-chloro-6-hydroxy-9H-purine. The catalytic activity of alumina prepared using the sol-gel method has larger Brunauer, Emmett, and Teller (BET) surface area and hence shows significantly greater catalytic activity than the commercially available alumina samples.

  DOI：

  10.1080/00397910903162791
• 作为产物：
  描述：

  2,6-二氯嘌呤 在 盐酸 作用下， 以 丙酮 为溶剂， 生成 2,6-二氯嘌呤盐酸盐
  参考文献：
  名称：

  N-Alkylation of 2,6-Dichloropurine Hydrochloride with a Variety of Alcohols over Alumina Catalyst

  摘要：

  2,6-Dichloropurine hydrochloride reacts with various types of alcohols using different alumina catalysts and converts into its N-9-alkyl-2-chloro-6-hydroxy-9H-purine products to an extent of 49-74%. The product selectivity depends on the stability of carbocation generated from the alcohol. More stable carbocation formulates both N-7 and N-9-alkyl-2,6-dichloropurine products, whereas the less stable carbocation results in exclusively N-9-alkyl-2-chloro-6-hydroxy-9H-purine. The catalytic activity of alumina prepared using the sol-gel method has larger Brunauer, Emmett, and Teller (BET) surface area and hence shows significantly greater catalytic activity than the commercially available alumina samples.

  DOI：

  10.1080/00397910903162791

文献信息

• Synthesis and Pharmacological Evaluation of Novel Non-nucleotide Purine Derivatives as P2X7 Antagonists for the Treatment of Neuroinflammation
  作者：Francesco Calzaferri、Paloma Narros-Fernández、Ricardo de Pascual、Antonio M.G. de Diego、Annette Nicke、Javier Egea、Antonio G. García、Cristóbal de los Ríos

  DOI：10.1021/acs.jmedchem.0c02145

  日期：2021.2.25

  Several P2X7 antagonists have been developed, though none of them reached clinical trials for this indication. In this work, we designed and synthesized novel blood–brain barrier (BBB)-permeable derivatives as potential P2X7 antagonists. They comprise purine or xanthine cores linked to an aryl group through different short spacers. Compounds were tested in YO-PRO-1 uptake assays and intracellular calcium

  ATP 门控 P2X7 嘌呤能受体 (P2X7) 参与许多神经退行性疾病 (NDD) 的发病机制。已经开发了几种 P2X7 拮抗剂，但没有一种达到该适应症的临床试验。在这项工作中，我们设计并合成了新型血脑屏障（BBB）渗透性衍生物作为潜在的 P2X7 拮抗剂。它们包含通过不同的短间隔基与芳基连接的嘌呤或黄嘌呤核心。在表达人 P2X7 的 HEK293 细胞系中的 YO-PRO-1 摄取测定和细胞内钙动力学、非洲爪蟾卵母细胞中的两电极电压钳记录以及小鼠腹膜巨噬细胞中的白细胞介素 1β 释放测定中测试了化合物。通过平行人工膜渗透性测定和 P-糖蛋白 ATP 酶活性评估 BBB 渗透性。二氯芳基嘌呤基乙醇具有一定的 P2X7 阻断作用，为化合物6 (2-(6-氯-9 H-嘌呤-9-基)-1-(2,4-二氯苯基)乙烷-1-酮)，命名为 ITH15004，是最有效的，选择性且 BBB 通透性拮抗剂。
• JP2008266201A
  申请人：——

  公开号：JP2008266201A

  公开（公告）日：2008-11-06
• N-Alkylation of 2,6-Dichloropurine Hydrochloride with a Variety of Alcohols over Alumina Catalyst
  作者：Harikrishna Tumma、N. Nagaraju、K. Vijayakumar Reddy

  DOI：10.1080/00397910903162791

  日期：2010.5.19

  2,6-Dichloropurine hydrochloride reacts with various types of alcohols using different alumina catalysts and converts into its N-9-alkyl-2-chloro-6-hydroxy-9H-purine products to an extent of 49-74%. The product selectivity depends on the stability of carbocation generated from the alcohol. More stable carbocation formulates both N-7 and N-9-alkyl-2,6-dichloropurine products, whereas the less stable carbocation results in exclusively N-9-alkyl-2-chloro-6-hydroxy-9H-purine. The catalytic activity of alumina prepared using the sol-gel method has larger Brunauer, Emmett, and Teller (BET) surface area and hence shows significantly greater catalytic activity than the commercially available alumina samples.