N6-[1-(S)-indanyl]adenosine | 96392-14-2

• 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: N6-[1-(S)-indanyl]adenosine
• 英文别名: (2R,3R,4S,5R)-2-[6-[[(1S)-2,3-dihydro-1H-inden-1-yl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 96392-14-2
• 化学式: C₁₉H₂₁N₅O₄
• 分子量: 383.407
• InChiKey: FSKMJUWPFLDDRS-BPAMBQHCSA-N

物化性质

• 沸点：
  723.3±70.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (S)-(+)-1-氨基茚满 、 6-氯嘌呤核苷 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 N6-[1-(S)-indanyl]adenosine
  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

文献信息

• N6-(1- and 2-benzocycloalkyl) adenosines, pharmaceutical compositions comprising the same and a process for the production thereof
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0144235A2

  公开（公告）日：1985-06-12

  Nekound 2-Benzocycloalkyl)adenosines of the formula and the pharmaceutically acceptable acid addition salts thereof, wherein R, is of the formula in which n is 0 or 1 are disclosed. The compounds have highly desirable central nervous system and cardiovascular properties. A process for the manufacture thereof and pharmaceutical compositions containing the same are also

  公开了式中 R 为 n 为 0 或 1 的 Nekound 2-苯并环烷基)腺苷及其药学上可接受的酸加成盐。 这些化合物具有非常理想的中枢神经系统和心血管特性。 还公开了其制造工艺和含有这些化合物的药物组合物。
• US4501735A
  申请人：——

  公开号：US4501735A

  公开（公告）日：1985-02-26