2-(3-phenylpropoxy)-Adenosine | 131865-80-0

• 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-(3-phenylpropoxy)-Adenosine
• 英文别名: 2-(3-phenylpropoxy)adenosine；2-phenylpropoxyadenosine；(2R,3R,4S,5R)-2-[6-amino-2-(3-phenylpropoxy)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 131865-80-0
• 化学式: C₁₉H₂₃N₅O₅
• 分子量: 401.422
• InChiKey: UDWLAWJOABGYPL-SCFUHWHPSA-N

物化性质

• 沸点：
  758.7±70.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  1-碘-3-苯基丙烷 在 氨 、 caesium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(3-phenylpropoxy)-Adenosine
  参考文献：
  名称：

  Structure−Activity Relationships of 2,N⁶,5‘-Substituted Adenosine Derivatives with Potent Activity at the A_2B Adenosine Receptor

  摘要：

  2, N-6, and 5'-substituted adenosine derivatives were synthesized via alkylation of 2-oxypurine nucleosides leading to 2-arylalkylether derivatives. 2-(3-(Indolyl)ethyloxy)adenosine 17 was examined in both binding and cAMP assays and found to be a potent agonist of the human A(2B)AR. Simplification, altered connectivity, and mimicking of the indole ring of 17 failed to maintain A2BAR potency. Introduction of N-6-ethyl or N-6-guanidino substitution, shown to favor A2BAR potency, failed to enhance potency in the 2-( 3-( indolyl)ethyloxy) adenosine series. Indole 5 ''- or 6 ''-halo substitution was favored at the A(2B)AR, but a 5'-N-ethylcarboxyamide did not further enhance potency. 2-(3 ''-(6 ''-Bromoindolyl)ethyloxy)adenosine 28 displayed an A(2B)AR EC50 value of 128 nM, that is, more potent than the parent 17 (299 nM) and similar to 5'-N-ethylcarboxamidoadenosine (140 nM). Compound 28 was a full agonist at A(2B) and A(2A)ARs and a low efficacy partial agonist at A(1) and A(3)ARs. Thus, we have identified and optimized 2-(2-arylethyl) oxo moieties in AR agonists that enhance A(2B)AR potency and selectivity.

  DOI：

  10.1021/jm061278q

文献信息

• 2-Aralkoxyadenosines: potent and selective agonists at the coronary artery A2 adenosine receptor
  作者：Masayuki Ueeda、Robert D. Thompson、Luis H. Arroyo、Ray A. Olsson

  DOI：10.1021/jm00108a015

  日期：1991.4

  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).
• 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