(2R,3R,4S,5R)-2-[6-(6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-7-ylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol | 132080-24-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (2R,3R,4S,5R)-2-[6-(6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-7-ylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 132080-24-1
• 化学式: C₂₀H₂₁N₅O₆
• 分子量: 427.417
• InChiKey: OEIZOYDXWDYTCO-CFIDXFGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-ylamine 、 6-氯嘌呤核苷 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 (2R,3R,4S,5R)-2-[6-(6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-7-ylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
  参考文献：
  名称：

  N6-Substituted adenosine receptor agonists: potential antihypertensive agents

  摘要：

  Adenosine is known to exert a wide range of pharmacological effects including hypotension. This effect of adenosine suggested that modified analogues of adenosine might provide useful antihypertensive agents. Thus, we prepared a series of novel N6-benzocycloalkyladenosines and studied their receptor binding and antihypertensive activity. The structure-activity relationship study shows that the adenosine analogues having the hydrophobic phenyl moiety one carbon away from the C6-nitrogen have modest affinity and selectivity for the A1 receptor, whereas those with the phenyl moiety two carbons away from the C6-nitrogen have excellent affinity and selectivity for the A1 receptor. Many of these analogues showed excellent antihypertensive activity with a wide range of effects on heart rate. There is no direct correlation between the receptor binding affinities and antihypertensive activity; however, it is more closely associated with A1 than A2 affinity. The bradycardic effect of these agonists seems to be due to the A1 affinity. From this set, compound 3 was further evaluated in secondary antihypertensive screens. It lowered the blood pressure dose dependently with effects lasting for over 20 h following administration of a 30 mg/kg dose. Compound 3 was also effective in lowering blood pressure in a renal hypertensive rat model. Thus, appropriately modified N6-substituted adenosines represent a novel class of antihypertensive agents.

  DOI：

  10.1021/jm00107a025