(2S,3S,4R,5R)-5-[6-amino-2-[2-(4-fluorophenyl)ethylamino]purin-9-yl]-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide | 120225-58-3

• 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: (2S,3S,4R,5R)-5-[6-amino-2-[2-(4-fluorophenyl)ethylamino]purin-9-yl]-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
• CAS: 120225-58-3
• 化学式: C₂₀H₂₄FN₇O₄
• 分子量: 445.453
• InChiKey: PVZXCHCLYHSMPG-QCUYGVNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  160
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-氯-2,3-o-异亚丙基腺苷酸-5-n-乙基羧酰胺 在 盐酸 作用下， 反应 4.0h， 生成 (2S,3S,4R,5R)-5-[6-amino-2-[2-(4-fluorophenyl)ethylamino]purin-9-yl]-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
  参考文献：
  名称：

  2-(Arylalkylamino)adenosin-5'-uronamides: a new class of highly selective adenosine A2 receptor ligands

  摘要：

  The synthesis and receptor-binding profiles at adenosine receptor subtypes for a series of 2-(arylalkylamino)-adenosin-5'-uronamides is described. Halogenated 2-phenethylamino analogues such as 3e show greater than 200-fold selectivity for the A2 receptor subtype on the basis of rat brain receptor binding. The general structure-activity relationship of this series of compounds is discussed both in terms of potency at A2 receptors as well as receptor subtype selectivity. It is possible to introduce a hydrophilic carboxyalkyl substituent to this series such as in CGS 21680A (3h) and still retain good potency and selectivity for A2 receptors. In addition, functional data in a perfused working rat heart model shows that these compounds possess full agonist properties at A2 receptors with 3h having a greater than 1500-fold separation between A2 (coronary vasodilatory) and A1 (negative chronotropic) receptor mediated events.

  DOI：

  10.1021/jm00169a015

文献信息

• HUTCHISON, ALAN J.;WILLIAMS, MICHAEL;JESUS, REYNALDA DE;RINA, YOKOYAMA;OE+, J. MED. CHEM., 33,(1990) N, C. 1919-1924
  作者：HUTCHISON, ALAN J.、WILLIAMS, MICHAEL、JESUS, REYNALDA DE、RINA, YOKOYAMA、OE+

  DOI：——

  日期：——
• 2-(Arylalkylamino)adenosin-5'-uronamides: a new class of highly selective adenosine A2 receptor ligands
  作者：Alan J. Hutchison、Michael Williams、Reynalda De Jesus、Rina Yokoyama、Howard H. Oei、Geetha R. Ghai、Randy L. Webb、Harry C. Zoganas、George A. Stone、Michael F. Jarvis

  DOI：10.1021/jm00169a015

  日期：1990.7

  The synthesis and receptor-binding profiles at adenosine receptor subtypes for a series of 2-(arylalkylamino)-adenosin-5'-uronamides is described. Halogenated 2-phenethylamino analogues such as 3e show greater than 200-fold selectivity for the A2 receptor subtype on the basis of rat brain receptor binding. The general structure-activity relationship of this series of compounds is discussed both in terms of potency at A2 receptors as well as receptor subtype selectivity. It is possible to introduce a hydrophilic carboxyalkyl substituent to this series such as in CGS 21680A (3h) and still retain good potency and selectivity for A2 receptors. In addition, functional data in a perfused working rat heart model shows that these compounds possess full agonist properties at A2 receptors with 3h having a greater than 1500-fold separation between A2 (coronary vasodilatory) and A1 (negative chronotropic) receptor mediated events.