N⁹-ethyl-2-(1-octyn-1-yl)adenine | 1610541-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N⁹-ethyl-2-(1-octyn-1-yl)adenine
• 英文别名: 9-Ethyl-2-oct-1-ynylpurin-6-amine；9-ethyl-2-oct-1-ynylpurin-6-amine
• CAS: 1610541-61-1
• 化学式: C₁₅H₂₁N₅
• 分子量: 271.365
• InChiKey: JFVSDLCYVKKSJL-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：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-octyn-1-yladenenosine 在 盐酸 、 水 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 N⁹-ethyl-2-(1-octyn-1-yl)adenine
  参考文献：
  名称：

  8-Substituted 2-alkynyl-N9-propargyladenines as A2A adenosine receptor antagonists

  摘要：

  Structure-activity relationships of 2-alkynyladenine derivatives were explored by varying substituents at the 9-, 8- and 2-positions of the purine moiety in order to optimize A(2A) adenosine receptor antagonist activity in vitro. A propargyl group at the 9-position was found to be important for A2A antagonist activity, and the introduction of a halogen, aryl, or heteroaryl at the 8-position further enhanced activity. A series of 8-substituted 2-alkynyl-N-9-propargyladenine derivatives exhibited potent antagonist activity, with IC50 values in the low nM range. Compound 4a from this series was found to be orally active at a dose of 3 mg/kg in a mouse catalepsy model and a 6-hydroxydopamine-lesioned rat model of Parkinson's disease. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.041

文献信息

• 8-Substituted 2-alkynyl-N9-propargyladenines as A2A adenosine receptor antagonists
  作者：Kazuki Endo、Kazuki Deguchi、Hirokazu Matsunaga、Kota Tomaya、Kohei Yamada

  DOI：10.1016/j.bmc.2014.04.041

  日期：2014.6

  Structure-activity relationships of 2-alkynyladenine derivatives were explored by varying substituents at the 9-, 8- and 2-positions of the purine moiety in order to optimize A(2A) adenosine receptor antagonist activity in vitro. A propargyl group at the 9-position was found to be important for A2A antagonist activity, and the introduction of a halogen, aryl, or heteroaryl at the 8-position further enhanced activity. A series of 8-substituted 2-alkynyl-N-9-propargyladenine derivatives exhibited potent antagonist activity, with IC50 values in the low nM range. Compound 4a from this series was found to be orally active at a dose of 3 mg/kg in a mouse catalepsy model and a 6-hydroxydopamine-lesioned rat model of Parkinson's disease. (C) 2014 Elsevier Ltd. All rights reserved.