2-[2-(thienyl)ethyloxy]adenosine | 131865-95-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-[2-(thienyl)ethyloxy]adenosine
• 英文别名: 2-[2-(thiophen-2-yl)ethoxy]-adenosine；2-[2-(2-thienyl)ethoxy]adenosine；(2R,3R,4S,5R)-2-(6-amino-2-(2-(thiophen-2-yl)ethoxy)-9H-purin-9-yl)-5-(hydroxymethyl)-tetrahydrofuran-3,4-diol；(2R,3R,4S,5R)-2-[6-amino-2-(2-thiophen-2-ylethoxy)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 131865-95-7
• 化学式: C₁₆H₁₉N₅O₅S
• 分子量: 393.423
• InChiKey: BVOKQKZIUWGDTK-SDBHATRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  177
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-噻吩乙醇 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 2-[2-(thienyl)ethyloxy]adenosine
  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-aralkyloxyadenosines, 2-alkoxyadenosines, and their analogs
  申请人：Moorman R. Allan

  公开号：US20060135466A1

  公开（公告）日：2006-06-22

  Provided is a method for the synthesis of an aralkyloxyadenosine or an alkoxyadenosine. The method includes protecting the hydroxyl sugar groups with a protecting group to produce a protected halogenated adenosine. The protected halogenated adenosine is alkoxylated, and the hydroxyl sugar groups of the protected halogenated adenosine are deprotected to provide the aralkyloxyadenosine or alkoxyadenosine.

  提供了一种合成芳基氧基腺苷或烷氧基腺苷的方法。该方法包括将糖基上的羟基保护起来以产生受保护的卤代腺苷。受保护的卤代腺苷被烷氧化，然后去除受保护的卤代腺苷的糖基上的羟基保护基，从而得到芳基氧基腺苷或烷氧基腺苷。
• [EN] SYNTHESIS OF 2-ARALKYLOXYADENOSINES, 2-ALKOXYADENOSINES, AND THEIR ANALOGS<br/>[FR] SYNTHESE DE 2-ARALKYLOXYADENOSINES, 2-ALKOXYADENOSINES, ET LEURS ANALOGUES
  申请人：KING PHARMACEUTICALS RES & DEV

  公开号：WO2005033121A3

  公开（公告）日：2005-07-28
• 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
• US5140015A
  申请人：——

  公开号：US5140015A

  公开（公告）日：1992-08-18