2-(1-octyn-1-yl)-N⁹-propargyladenine | 1379508-84-5

• 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: 2-(1-octyn-1-yl)-N⁹-propargyladenine
• 英文别名: 2-Oct-1-ynyl-9-prop-2-ynylpurin-6-amine；2-oct-1-ynyl-9-prop-2-ynylpurin-6-amine
• CAS: 1379508-84-5
• 化学式: C₁₆H₁₉N₅
• 分子量: 281.36
• InChiKey: OTYGGGUXFQSYSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-octyn-1-yl)-N⁹-propargyladenine 在 N-氯代丁二酰亚胺 、 potassium acetate 作用下， 以 氯仿 为溶剂， 反应 30.0h， 以55%的产率得到8-chloro-2-(1-octyn-1-yl)-N⁹-propargyladenine
  参考文献：
  名称：

  NOVEL 2-ALKYNYL-N9-PROPARGYLADENINE AND MEDICINAL USE THEREOF

  摘要：

  本发明涉及一种新型2-炔基-N9-丙炔基腺嘌呤，其化学式为（I），其中R1代表卤素原子、呋喃基或三唑基；R2和R3分别代表氢原子或C1-8烷基，或通过相互结合形成环烷基；X代表氢原子或羟基，或其药学上可接受的盐。该化合物作为帕金森综合症治疗剂具有更强和更持久的效果。

  公开号：

  US20130245046A1
• 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 12.5h， 生成 2-(1-octyn-1-yl)-N⁹-propargyladenine
  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

• NOVEL 2-ALKYNYL-N9-PROPARGYLADENINE AND MEDICINAL USE THEREOF
  申请人：Endo Kazuki

  公开号：US20130245046A1

  公开（公告）日：2013-09-19

  In the present invention, a novel 2-alkynyl-N9-propargyladenine represented by formula (I) wherein R 1 represents a halogen atom, a furyl group, or a triazolyl group; R 2 and R 3 each represents a hydrogen atom or a C1-8 alkyl group, or form a cycloalkyl group by bonding to each other; and X represents a hydrogen atom or a hydroxyl group, or a pharmaceutically acceptable salt thereof, has a stronger and longer-lasting effect as a therapeutic agent for Parkinsonian syndromes.

  本发明涉及一种新型2-炔基-N9-丙炔基腺嘌呤，其化学式为（I），其中R1代表卤素原子、呋喃基或三唑基；R2和R3分别代表氢原子或C1-8烷基，或通过相互结合形成环烷基；X代表氢原子或羟基，或其药学上可接受的盐。该化合物作为帕金森综合症治疗剂具有更强和更持久的效果。
• US8791126B2
  申请人：——

  公开号：US8791126B2

  公开（公告）日：2014-07-29
• 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.