(2S,3S,4R,5R)-5-[6-Amino-2-(methyl-phenethyl-amino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid ethylamide; hydrochloride | 127258-40-6

• 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-(methyl-phenethyl-amino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid ethylamide; hydrochloride
• CAS: 127258-40-6
• 化学式: C₂₁H₂₇N₇O₄*ClH
• 分子量: 477.951
• InChiKey: ICNCJILLQBIURZ-GDGFGLPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.26
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  151.65
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  2-氯腺嘌呤核苷 在 盐酸 、 氢氧化钾 、 potassium permanganate 、 氯化亚砜 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 95.0h， 生成 (2S,3S,4R,5R)-5-[6-Amino-2-(methyl-phenethyl-amino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid ethylamide; hydrochloride
  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