(2R,3R,4S,5R)-2-[2-Chloro-6-((S)-1-methyl-2-phenyl-ethylamino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol | 23559-45-7

• 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-[2-Chloro-6-((S)-1-methyl-2-phenyl-ethylamino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol
• 英文别名: (2R,3R,4S,5R)-2-[2-chloro-6-[[(2S)-1-phenylpropan-2-yl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 23559-45-7
• 化学式: C₁₉H₂₂ClN₅O₄
• 分子量: 419.868
• InChiKey: XQOFIPOEIPAISE-QHOAOGIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• 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：

  (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate 、 右旋苯丙胺 在 氨 、 N,N-二异丙基乙胺 作用下， 生成 (2R,3R,4S,5R)-2-[2-Chloro-6-((S)-1-methyl-2-phenyl-ethylamino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  Activity of N6-substituted 2-chloroadenosines at A1 and A2 adenosine receptors

  摘要：

  Radioligand binding studies of N6-substituted adenosines at the A1 and A2 adenosine receptors of rat brain cortex and rat brain striatum, respectively, show that a 2-chloro substituent does not consistently change the affinity or the selectivity of these analogues for the A1 receptor. A 2-chloro substituent lowers the characteristic stereoselectivity of the A1 receptor toward the R diasteromer of N6-(1-phenyl-2-propyl)adenosine. A 2-chloro substituent consistently increases potency of N6-substituted adenosines as agonists at an adenosine A2 receptor stimulatory to adenylate cyclase in PC12 cell membranes.

  DOI：

  10.1021/jm00116a007

文献信息

• Activity of N6-substituted 2-chloroadenosines at A1 and A2 adenosine receptors
  作者：Robert D. Thompson、Sherrie Secunda、John W. Daly、Ray A. Olsson

  DOI：10.1021/jm00116a007

  日期：1991.12

  Radioligand binding studies of N6-substituted adenosines at the A1 and A2 adenosine receptors of rat brain cortex and rat brain striatum, respectively, show that a 2-chloro substituent does not consistently change the affinity or the selectivity of these analogues for the A1 receptor. A 2-chloro substituent lowers the characteristic stereoselectivity of the A1 receptor toward the R diasteromer of N6-(1-phenyl-2-propyl)adenosine. A 2-chloro substituent consistently increases potency of N6-substituted adenosines as agonists at an adenosine A2 receptor stimulatory to adenylate cyclase in PC12 cell membranes.