6-chloro-9-(1,2,3,4-tetrahydronaphthalen-1-yl)-9H-purine | 944450-61-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-chloro-9-(1,2,3,4-tetrahydronaphthalen-1-yl)-9H-purine
• 英文别名: 6-Chloro-9-(1,2,3,4-tetrahydronaphthalen-1-yl)purine
• CAS: 944450-61-7
• 化学式: C₁₅H₁₃ClN₄
• 分子量: 284.748
• InChiKey: HOWPUFZQOUIIBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-9-(1,2,3,4-tetrahydronaphthalen-1-yl)-9H-purine 在 sodium hydroxide 作用下， 生成 9-(1,2,3,4-Tetrahydro-naphthalen-1-yl)-1,9-dihydro-purin-6-one
  参考文献：
  名称：

  Synthesis and structure–activity relationships of guanine analogues as phosphodiesterase 7 (PDE7) inhibitors

  摘要：

  The synthesis of a novel series of guanine analogues is reported. The compounds have been assessed in vitro and some analogues have been found to be inhibitors of phosphodiesterase type 7 (PDE7). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00125-1
• 作为产物：
  描述：

  6-氯嘌呤 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 生成 6-chloro-9-(1,2,3,4-tetrahydronaphthalen-1-yl)-9H-purine
  参考文献：
  名称：

  Synthesis and structure–activity relationships of guanine analogues as phosphodiesterase 7 (PDE7) inhibitors

  摘要：

  The synthesis of a novel series of guanine analogues is reported. The compounds have been assessed in vitro and some analogues have been found to be inhibitors of phosphodiesterase type 7 (PDE7). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00125-1

文献信息

• Synthesis of Novel Purine-Based Coxsackievirus Inhibitors Bearing Polycylic Substituents at the N-9 Position
  作者：Milan Dejmek、Michal Šála、Pavla Plačková、Hubert Hřebabecký、Laura Mascarell Borredà、Johan Neyts、Martin Dračínský、Eliška Procházková、Petr Jansa、Pieter Leyssen、Helena Mertlíková-Kaiserová、Radim Nencka

  DOI：10.1002/ardp.201300431

  日期：2014.7

  The synthesis of a novel library of purine derivatives bearing various bicyclic and polycylic substituents at the N‐9 position is described. The series includes norbornanes, bicyclo[2.2.2]octanes, and bicyclo[3.2.1]octanes attached at the bridgehead position as well as bicyclo[3.1.1]heptanes, tetrahydro‐1‐naphthalenes, and adamantanes bonded either directly or via a linear chain to the 6‐chloropurine

  描述了在 N-9 位置带有各种双环和多环取代基的新型嘌呤衍生物库的合成。该系列包括在桥头位置连接的降冰片烷、双环[2.2.2]辛烷和双环[3.2.1]辛烷以及直接或通过连接的双环[3.1.1]庚烷、四氢-1-萘和金刚烷6-氯嘌呤核碱基的线性链。许多制备的衍生物对肠道病毒具有显着的活性。尽管试图将针对小核糖核酸病毒的活性与其磷脂酰肌醇 4-激酶 KIIIβ 抑制活性相关联，但很明显，这种宿主因子的抑制不能解释观察到的抗病毒效力。
• Mitsunobu Coupling of Nucleobases and Alcohols:  An Efficient, Practical Synthesis for Novel Nonsugar Carbon Nucleosides
  作者：Weibing Lu、Sujata Sengupta、Jeffrey L. Petersen、Novruz G. Akhmedov、Xiaodong Shi

  DOI：10.1021/jo070515+

  日期：2007.6.1

  A simple facile synthesis of substituted purine derivatives has been developed by using Mitsunobu conditions for an alcohol and a respective nucleobase. A wide range of alcohols produces good to excellent yield (> 90%). The resulting purine analogues show good regioselectivity with N-9 substitution as the dominant products in most of the cases. Application of diastereospecific alcohols reveals a complete inversion of the carbon stereogenic center giving a single diastereomer. More than two dozen novel nucleobase derivatives have been prepared in high yield.