(2R,3R,4S,5R)-2-[6-amino-2-(4-cyclohexylbutoxy)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol | 131933-20-5

• 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: (2R,3R,4S,5R)-2-[6-amino-2-(4-cyclohexylbutoxy)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 131933-20-5
• 化学式: C₂₀H₃₁N₅O₅
• 分子量: 421.497
• InChiKey: OXOBGRYXRGZAJU-NVQRDWNXSA-N

物化性质

• 熔点：
  191 °C
• 沸点：
  722.9±70.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  4-环己基-1-丁醇 在 正丁基锂 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 生成 (2R,3R,4S,5R)-2-[6-amino-2-(4-cyclohexylbutoxy)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
  参考文献：
  名称：

  2-Alkoxyadenosines: 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 activity of a series of 24 2-alkoxyadenosines at the A1 and A2 adenosine receptors of, respectively, the atrioventricular node (conduction block) and coronary arteries (vasodilation). Activities are low at the A1 receptor and do not show a clear relationship to the size or hydrophobicity of the C-2 substituent. All the analogues are more potent at the A2 receptor, activity varying directly with the size and hydrophobicity of the alkyl group. The most potent analogue in this series, 2-(2-cyclohexylethoxy)adenosine, has an EC50 of 1 nM for coronary vasodilation and is 8700-fold selective for the A2 receptor.

  DOI：

  10.1021/jm00108a014

文献信息

• UEEDA, MASAYUKI;THOMPSON, ROBERT D.;ARROYO, LUIS H.;OLSSON, RAY A., J. MED. CHEM., 34,(1991) N, C. 1334-1339
  作者：UEEDA, MASAYUKI、THOMPSON, ROBERT D.、ARROYO, LUIS H.、OLSSON, RAY A.

  DOI：——

  日期：——
• 2-Alkoxyadenosines: 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/jm00108a014

  日期：1991.4

  A Langendorff guinea pig heart preparation served for the assay of agonist activity of a series of 24 2-alkoxyadenosines at the A1 and A2 adenosine receptors of, respectively, the atrioventricular node (conduction block) and coronary arteries (vasodilation). Activities are low at the A1 receptor and do not show a clear relationship to the size or hydrophobicity of the C-2 substituent. All the analogues are more potent at the A2 receptor, activity varying directly with the size and hydrophobicity of the alkyl group. The most potent analogue in this series, 2-(2-cyclohexylethoxy)adenosine, has an EC50 of 1 nM for coronary vasodilation and is 8700-fold selective for the A2 receptor.