2-(4-Pyridyl)adenine | 135280-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(4-Pyridyl)adenine
• 英文别名: 2-pyridin-4-yl-7H-purin-6-amine
• CAS: 135280-91-0
• 化学式: C₁₀H₈N₆
• 分子量: 212.214
• InChiKey: RHXNIWQLYSHZAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-Pyridyl)adenine 、 4-二苯基甲基-1-(2,3-环氧丙基)哌嗪 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以28%的产率得到1-(6-Amino-2-pyridin-4-yl-purin-9-yl)-3-(4-benzhydryl-piperazin-1-yl)-propan-2-ol
  参考文献：
  名称：

  Synthesis and Structure-Activity Relationships of 6-Heterocyclic-Substituted Purines as Inactivation Modifiers of Cardiac Sodium Channels

  摘要：

  Purine-based analogs of SDZ 211-500 (5) were prepared and evaluated as inactivation modifiers of guinea pig or human cardiac sodium (Na) channels expressed in Xenopus oocytes. Substances which remove or slow the Na channel inactivation process in cardiac tissue are anticipated to prolong the effective refractory period and increase inotropy and thus have potential utility as antiarrhythmic agents. Heterocyclic substitution at the 6-position of the purine ring resulted in compounds with increased Na activity and potency, with 5-membered heterocycles being optimal. Only minor modifications to the benzhydrylpiperazine side chain were tolerated. Selected compounds which delayed the inactivation of Na channels were found to increase refractoriness and contractility in a rabbit Langendorff heart model, consistent with the cellular mechanism. Activity in both the oocyte and rabbit heart assays was specific to the S enantiomers. Preliminary in vivo activity has been demonstrated following intravenous infusion. The most promising compound on the basis of in vitro data is the formylpyrrole (S)-74, which is 25-fold more potent than DPI 201-106 (1) in the human heart Na channel assay.

  DOI：

  10.1021/jm00014a011
• 作为产物：
  描述：

  4,6-Diamino-5-phenylazo-2-(4-pyridyl)pyrimidine 在 镍 盐酸 、 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-(4-Pyridyl)adenine
  参考文献：
  名称：

  A Convenient Synthesis of 8-Alkyl- and 8-Alkylthio-2-(4-pyridyl)adenines

  摘要：

  通过将4,5,6-三氨基嘧啶4与酸酐、酸或二甲基甲酰胺二甲基乙缩醛反应，制备了几种8-烷基-2-(4-吡啶基)腺嘌呤类似物5。8-巯基-2-(4-吡啶基)腺嘌呤(6)是通过将4与O-钾O-乙基二硫代碳酸酯处理制备的，然后进行烷基化得到8-烷硫基腺嘌呤衍生物7。

  DOI：

  10.1055/s-1991-26422

文献信息

• A Convenient Synthesis of 8-Alkyl- and 8-Alkylthio-2-(4-pyridyl)adenines
  作者：Balder Singh、George Y. Lesher

  DOI：10.1055/s-1991-26422

  日期：——

  Several 8-alkyl-2-(4-pyridyl)adenine analogs 5 were prepared by reacting 4,5,6-triaminopyrimidine 4 with acid anhydrides, acids or dimethylformamide dimethyl acetal. 8-Mercapto-2-(4-pyridyl)-adenine (6), prepared by treating 4 with O-potassium O-ethyl dithiocarbonate was alkylated to give 8-alkylthioadenine derivatives 7.

  通过将4,5,6-三氨基嘧啶4与酸酐、酸或二甲基甲酰胺二甲基乙缩醛反应，制备了几种8-烷基-2-(4-吡啶基)腺嘌呤类似物5。8-巯基-2-(4-吡啶基)腺嘌呤(6)是通过将4与O-钾O-乙基二硫代碳酸酯处理制备的，然后进行烷基化得到8-烷硫基腺嘌呤衍生物7。
• Synthesis and Structure-Activity Relationships of 6-Heterocyclic-Substituted Purines as Inactivation Modifiers of Cardiac Sodium Channels
  作者：Kimberly G. Estep、Kurt A. Josef、Edward R. Bacon、Philip M. Carabateas、Squire Rumney、Garry M. Pilling、Douglas S. Krafte、Walter A. Volberg、Kathleen Dillon、Nancy Dugrenier、G. Maurice Briggs、Paul C. Canniff、William P. Gorczyca、Gerald P. Stankus、Alan M. Ezrin

  DOI：10.1021/jm00014a011

  日期：1995.7

  Purine-based analogs of SDZ 211-500 (5) were prepared and evaluated as inactivation modifiers of guinea pig or human cardiac sodium (Na) channels expressed in Xenopus oocytes. Substances which remove or slow the Na channel inactivation process in cardiac tissue are anticipated to prolong the effective refractory period and increase inotropy and thus have potential utility as antiarrhythmic agents. Heterocyclic substitution at the 6-position of the purine ring resulted in compounds with increased Na activity and potency, with 5-membered heterocycles being optimal. Only minor modifications to the benzhydrylpiperazine side chain were tolerated. Selected compounds which delayed the inactivation of Na channels were found to increase refractoriness and contractility in a rabbit Langendorff heart model, consistent with the cellular mechanism. Activity in both the oocyte and rabbit heart assays was specific to the S enantiomers. Preliminary in vivo activity has been demonstrated following intravenous infusion. The most promising compound on the basis of in vitro data is the formylpyrrole (S)-74, which is 25-fold more potent than DPI 201-106 (1) in the human heart Na channel assay.