3'-deoxy-2',5'-di-O-acetyl-6-iodopurine-9-β-D-riboside | 171501-70-5

• 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: 3'-deoxy-2',5'-di-O-acetyl-6-iodopurine-9-β-D-riboside
• 英文别名: [(2S,4R,5R)-4-acetyloxy-5-(6-iodopurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 171501-70-5
• 化学式: C₁₄H₁₅IN₄O₅
• 分子量: 446.201
• InChiKey: VALQJCPWWWRERQ-IMSIIYSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  右旋苯丙胺 、 3'-deoxy-2',5'-di-O-acetyl-6-iodopurine-9-β-D-riboside 以 乙醇 为溶剂， 反应 336.0h， 以37%的产率得到3'-deoxy-N⁶(S)-(phenylisopropyl)adenosine
  参考文献：
  名称：

  Ribose-Modified Adenosine Analogs as Potential Partial Agonists for the Adenosine Receptor

  摘要：

  We have adopted a practical three-step route for the synthesis of 2'- and 3'-deoxy analogues of N-6-substituted adenosines: protection of the hydroxyl groups, replacement of the N-6-amino by a better leaving group, and combined deprotection and N-6-amination in the last step. This route was used to synthesize deoxy analogues of CPA, CHA, and R- and S-PIA. The compounds were tested on the adenosine A(1) and A(2a) receptors in our search for partial agonists for these receptors. The GTP shift was used as an in vitro measure for the intrinsic activity of these compounds; the in vivo intrinsic activities of the deoxy analogues of CPA and R-PIA were determined in the rat cardiovascular system. Thus, it was shown that the hydroxyl groups are determinants for the affinity and intrinsic activity of these analogues. Removal of the 2'-and 3'-hydroxyl groups affects affinity and intrinsic activity, whereas removal of the 5'-hydroxyl group decreases only affinity.

  DOI：

  10.1021/jm00020a014
• 作为产物：
  描述：

  2',5'-di-O-acetyl-3'-deoxyadenosine 在 二碘甲烷 、 亚硝酸异戊酯 作用下， 反应 2.0h， 以63%的产率得到3'-deoxy-2',5'-di-O-acetyl-6-iodopurine-9-β-D-riboside
  参考文献：
  名称：

  Ribose-Modified Adenosine Analogs as Potential Partial Agonists for the Adenosine Receptor

  摘要：

  We have adopted a practical three-step route for the synthesis of 2'- and 3'-deoxy analogues of N-6-substituted adenosines: protection of the hydroxyl groups, replacement of the N-6-amino by a better leaving group, and combined deprotection and N-6-amination in the last step. This route was used to synthesize deoxy analogues of CPA, CHA, and R- and S-PIA. The compounds were tested on the adenosine A(1) and A(2a) receptors in our search for partial agonists for these receptors. The GTP shift was used as an in vitro measure for the intrinsic activity of these compounds; the in vivo intrinsic activities of the deoxy analogues of CPA and R-PIA were determined in the rat cardiovascular system. Thus, it was shown that the hydroxyl groups are determinants for the affinity and intrinsic activity of these analogues. Removal of the 2'-and 3'-hydroxyl groups affects affinity and intrinsic activity, whereas removal of the 5'-hydroxyl group decreases only affinity.

  DOI：

  10.1021/jm00020a014