腺苷,2-(苯基甲氧基)- | 131865-78-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 腺苷,2-(苯基甲氧基)-
• 英文名称: 2-(phenylmethoxy)-Adenosine
• 英文别名: 2-benzyloxyadenosine；(2R,3R,4S,5R)-2-(6-amino-2-phenylmethoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 131865-78-6
• 化学式: C₁₇H₁₉N₅O₅
• 分子量: 373.368
• InChiKey: FUODJAMHKWCPRT-XNIJJKJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-chloro-2',3'-O-(ethoxymethylidene) adenosine 在 正丁基锂 、 甲酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.25h， 生成 腺苷,2-(苯基甲氧基)-
  参考文献：
  名称：

  2-Aralkoxyadenosines: potent and selective agonists at the coronary artery A2 adenosine receptor

  摘要：

  A Langendorff guinea pig heart preparation served for the assay of agonist potency of a series of 26 2-aralkoxyadenosines at the A1 and A2 receptors of, respectively, the atrioventricular node (conduction block) and coronary arteries (vasodilation). All of the analogues are weak agonists at the A1 receptor, requiring concentrations > 9-mu-M to cause second degree heart block. At the A2 receptor 2-phenethoxyadenosine is the most potent of the 2-phenylalkyladenosines. The activity of ring-substituted (F, Cl, CH3, and OCH3) 2-phenethoxyadenosines increases ortho < meta < para. The EC50s of coronary vasoactivity of several para-substituted analogues are in the subnanomolar range. The most potent analogue, 2-[2-(4-methylphenyl)ethoxy]adenosine 19, has an EC50 for coronary vasodilation of 190 pM and an A1/A2 selectivity ratio of 44000. Aryl groups such as thienyl, indoloyl, or naphthyl also support A2 agonist activity. Although 2-oxoadenosine is 3 times more vasoactive than 2-aminoadenosine, the activities of the phenyl derivatives are markedly different; 2-phenoxyadenosine is 23 times weaker than 2-(phenylamino)adenosine (CV-1808).

  DOI：

  10.1021/jm00108a015

文献信息

• Synthesis of 2-aralkoxyadenosines and 2-alkoxyadenosines
  申请人：——

  公开号：US20030199686A1

  公开（公告）日：2003-10-23

  The invention provides new methods for synthesis of 2-aralkyloxyadenosines and 2-alkoxyadenosines. The invention is particularly useful for synthesis of 2-[2-(4-chlorophenyl)ethoxy]adenosine. Preferred methods of the invention include activating a guanosine compound followed by hydrolysis; alkylating the hydrolyzed compound with subsequent animation to provide a 2-aralkyloxyadenosine or a 2-alkoxyadenosine compound.

  这项发明提供了合成2-芳基氧基腺苷和2-烷氧基腺苷的新方法。该发明特别适用于合成2-[2-(4-氯苯基)乙氧基]腺苷。该发明的首选方法包括激活鸟苷化合物，然后进行水解；烷基化水解后的化合物，随后进行胺化，以提供2-芳基氧基腺苷或2-烷氧基腺苷化合物。
• EP0515514A4
  申请人：——

  公开号：EP0515514A4

  公开（公告）日：1993-01-13
• 2-ARALKOXY AND 2-ALKOXY ADENOSINE DERIVATIVES AS CORONARY VASODILATORS AND ANTIHYPERTENSIVE AGENTS
  申请人：WHITBY RESEARCH, Inc.

  公开号：EP0515514A1

  公开（公告）日：1992-12-02
• SYNTHESIS OF 2-ARALKOXY ADENOSINES AND 2-ALKOXYADENOSINES
  申请人：King Pharmaceuticals Research and Development Inc.

  公开号：EP1446413A1

  公开（公告）日：2004-08-18
• EP1446413A4
  申请人：——

  公开号：EP1446413A4

  公开（公告）日：2007-10-17