2-[2-(1-naphthyl)ethyloxy]adenosine | 131865-98-0

• 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-(1-naphthyl)ethyloxy]adenosine
• 英文别名: 2-[2-(1-naphthyl)ethoxy]adenosine；(2R,3R,4S,5R)-2-[6-amino-2-(2-naphthalen-1-ylethoxy)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 131865-98-0
• 化学式: C₂₂H₂₃N₅O₅
• 分子量: 437.455
• InChiKey: YYSHRNQNOWOELU-QTQZEZTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 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 2-[2-(1-naphthyl)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

• 2-aralkoxy and 2-alkoxy adenosine derivatives as coronary vasodilators
  申请人：Whitby Research, Inc.

  公开号：US05140015A1

  公开（公告）日：1992-08-18

  Compounds are disclosed having the formulae: ##STR1## wherein R.sub.1 is selected from the group, consisting of radicals represented by the general formulae: ##STR2## wherein Y is selected from the group consisting of lower alkyl, lower alkoxy, and halogen; Z is oxygen, sulfur or --NH, Q is --CH or nitrogen; a is zero or an integer of from one to three; and wherein, R.sub.2 is selected from the group consisting of hydrogen and straight chain, branched and cyclic hydrocarbyl radicals having from one to four carbon atoms, and optionally substituted with a hydroxyl radical; and wherein X is two hydrogen atoms or oxygen and B is selected from oxygen and nitrogen, and pharmaceutically acceptable salts thereof, with the proviso that when X is two hydrogen atoms, B is oxygen, and with the further proviso that when B is oxygen then R.sub.1 cannot be a phenyl or a substituted phenyl radical. Pharmaceutical preparations using these compounds and a method for inducing an adenosine response mediated by the adenosine A.sub.2 receptor by administering these compounds are also disclosed.

  揭示了具有以下结构的化合物：其中R.sub.1是从以下基团中选择的，该基团由一般式代表的基团组成：其中Y是从以下基团中选择的，该基团由较低烷基、较低烷氧和卤素组成；Z是氧、硫或--NH；Q是--CH或氮；a是零或从一到三的整数；其中，R.sub.2是从氢和直链、支链和环烃基基团中选择的，该基团含有从一个到四个碳原子，并且可选地被一个羟基基团取代；其中X是两个氢原子或氧，B是氧和氮中选择的，并且其药学上可接受的盐，但有一个条件是当X是两个氢原子时，B是氧，还有一个条件是当B是氧时，R.sub.1不能是苯基或取代苯基基团。还揭示了使用这些化合物的药物制剂以及通过给予这些化合物诱导由腺苷A.sub.2受体介导的腺苷反应的方法。
• 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
• USRE36494E
  申请人：——

  公开号：USRE36494E

  公开（公告）日：2000-01-11