2-[2-(2-萘基)乙氧基]腺苷 | 131865-99-1

• 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: 2-[2-(2-萘基)乙氧基]腺苷
• 英文名称: 2-[2-(2-Naphthylethoxy)adenosine]
• 英文别名: WRC-0018；2-[2-(2-Naphthalenyl)ethoxy]adenosine；(2R,3R,4S,5R)-2-[6-amino-2-(2-naphthalen-2-ylethoxy)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 131865-99-1
• 化学式: C₂₂H₂₃N₅O₅
• 分子量: 437.455
• InChiKey: LCDBQJZQQFLFGG-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-(2-萘基)乙氧基]腺苷
  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。
• 脈管再生手順の後の再狭窄を防止するための組成物および方法
  申请人：ディスカバリー セラピューティクス,インコーポレイテッド

  公开号：JP2002505687A

  公开（公告）日：2002-02-19

  \n (57)【要約】\n本発明において、脈管再生手順の後の再狭窄を減少または予防する方法が提供される。アデノシンA2Aレセプターの選択的刺激がそのような再狭窄を減少または予防し得ることが、ここで見いだされた。本方法は、以下のいずれかにより達成され得る：(a)選択的アデノシンA2Aレセプターアゴニストの投与、(b)選択的アデノシンA2Aレセプターアゴニストまたは非選択的アデノシンアゴニストのいずれかと組み合わせた選択的アデノシンA1アンタゴニストの投与、または(c)内在的に放出されるアデノシンによるアデノシンA1レセプターの活性化を妨害するための選択的アデノシンA1アンタゴニストの投与。本発明はまた、アデノシンA2Aレセプターの選択的刺激に依存する改善された外科的手順に関する。\n

  \n (57) [摘要]本发明提供了减少或预防血管再生术后再狭窄的方法。本发明发现，选择性刺激腺苷 A2A 受体可减少或预防此类再狭窄。该方法可通过以下任一方法实现：(a) 给予选择性腺苷 A2A 受体激动剂；(b) 选择性腺苷 A1 拮抗剂与选择性腺苷 A2A 受体激动剂或非选择性腺苷激动剂联合使用；或 (c)使用选择性腺苷 A1 拮抗剂干扰内源性释放的腺苷对腺苷 A1 受体的激活。本发明还涉及依赖于选择性刺激腺苷 A2A 受体的改良外科手术。\n
• Compositions and methods for preventing restenosis following revascularization procedures
  申请人：Discovery Therapeutics, Inc.

  公开号：US20010009907A1

  公开（公告）日：2001-07-26

  In the present invention, a method is provided which reduces or prevents restenosis following revascularization procedures. It has now been found that selective stimulation of adenosine A 2A receptors can reduce or prevent such restenosis. This method may be achieved either by: (a) the administration of selective adenosine A 2A receptor agonists, (b) the administration of a selective adenosine A 1 antagonist in combination with either a selective adenosine A 2A receptor agonist or a non-selective adenosine agonist, or (c) the administration of a selective adenosine A 1 antagonist in order to block adenosine A 1 receptor activation by endogenously-released adenosine. The present invention is also directed to an improved surgical procedure that relies upon selective stimulation of adenosine A 2A receptors.

  本发明提供了一种方法，可减少或防止血管再通手术后的再狭窄。现已发现，选择性刺激腺苷 A 2A 受体可减少或预防此类再狭窄。这种方法可以通过以下方式实现(a) 给予选择性腺苷 A 2A 受体激动剂，(b) 使用选择性腺苷 A 1 拮抗剂与选择性腺苷 A 2A 受体激动剂或非选择性腺苷激动剂，或 (c) 使用选择性腺苷 A 1 拮抗剂，以阻断腺苷 A 1 受体被内源性释放的腺苷激活。本发明还涉及一种改进的外科手术方法，它依赖于选择性刺激腺苷 A 2A 受体。
• 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