6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-ylamine | 907973-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-ylamine
• 英文别名: 6,7-Dihydro-5H-indeno[5,6-d][1,3]dioxol-5-ylamin；6,7-Dihydro-5H-indeno[5,6-D][1,3]dioxol-5-amine；6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-7-amine
• CAS: 907973-38-0
• 化学式: C₁₀H₁₁NO₂
• mdl: MFCD07373966
• 分子量: 177.203
• InChiKey: JIXKYMZRBCSGBI-UHFFFAOYSA-N

物化性质

• 沸点：
  293.5±39.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  6,7-dihydro-indeno[5,6-d][1,3]dioxol-5-one oxime 在 sodium amalgam 、 溶剂黄146 作用下， 生成 6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-ylamine
  参考文献：
  名称：

  Trikojus; White, Journal and Proceedings - Royal Society of New South Wales, 1940, vol. 74, p. 82,86

  摘要：

  DOI：

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。
• TRIVEDI, B. K.;BLANKLEY, C. J.;BRISTOL, J. A.;HAMILTON, H. W.;PATT, W. C.+, J. MED. CHEM., 34,(1991) N, C. 1043-1049
  作者：TRIVEDI, B. K.、BLANKLEY, C. J.、BRISTOL, J. A.、HAMILTON, H. W.、PATT, W. C.+

  DOI：——

  日期：——
• Trikojus; White, Journal and Proceedings - Royal Society of New South Wales, 1940, vol. 74, p. 82,86
  作者：Trikojus、White

  DOI：——

  日期：——
• N6-Substituted adenosine receptor agonists: potential antihypertensive agents
  作者：B. K. Trivedi、C. J. Blankley、J. A. Bristol、H. W. Hamilton、W. C. Patt、W. J. Kramer、S. A. Johnson、R. F. Bruns、D. M. Cohen、M. J. Ryan

  DOI：10.1021/jm00107a025

  日期：1991.3

  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.