9-<1-hydroxy-2(R)-octyl>adenine | 143788-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-<1-hydroxy-2(R)-octyl>adenine
• 英文别名: 9-(1-hydroxy-2(R)-octyl)adenine；2-(6-Amino-purin-9-yl)-octan-1-ol；(2R)-2-(6-aminopurin-9-yl)octan-1-ol
• CAS: 143788-70-9
• 化学式: C₁₃H₂₁N₅O
• 分子量: 263.343
• InChiKey: YXBJLOKJVFLXCO-SNVBAGLBSA-N

物化性质

• 沸点：
  475.7±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-<1-hydroxy-2(R)-octyl>adenine 在 (diethylamido)sulfur trifluoride 作用下， 以 二氯甲烷 为溶剂， 以38%的产率得到9-<1-fluoro-2(R)-octyl>adenine
  参考文献：
  名称：

  Adenosine deaminase inhibitors. Synthesis and biological evaluation of C1' and nor-C1' derivatives of (+)-erythro-9-[2(S)-hydroxy-3(R)-nonyl]adenine

  摘要：

  The synthesis of various chiral derivatives of (+)-erythro-9-(2-hydroxy-3-nonyl)adenine, (+)-EHNA, from (2S,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol by condensation with 5-amino-4,6-dichloropyrimidine is described. The compounds synthesized were Cl'- and nor-Cl'-(+)-EHNA derivatives. When tested with calf spleen ADA, Cl'-OH- and nor-Cl'-(+)-EHNA had comparable inhibitory activity that was 1 order of magnitude lower than that of (+)-EHNA. Potency was reduced further in nor-Cl' derivatives.

  DOI：

  10.1021/jm00100a025
• 作为产物：
  描述：

  magnesium,pentane,chloride 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 sodium periodate 、 sodium dihydrogenphosphate 、 lithium aluminium tetrahydride 、 甲酸 、 sodium azide 、 dilithium tetrachlorocuprate 、 三正丁胺 、 氨 作用下， 以 乙醚 、 二氯甲烷 、 戊醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.25h， 生成 9-<1-hydroxy-2(R)-octyl>adenine
  参考文献：
  名称：

  Adenosine deaminase inhibitors. Synthesis and biological evaluation of C1' and nor-C1' derivatives of (+)-erythro-9-[2(S)-hydroxy-3(R)-nonyl]adenine

  摘要：

  The synthesis of various chiral derivatives of (+)-erythro-9-(2-hydroxy-3-nonyl)adenine, (+)-EHNA, from (2S,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol by condensation with 5-amino-4,6-dichloropyrimidine is described. The compounds synthesized were Cl'- and nor-Cl'-(+)-EHNA derivatives. When tested with calf spleen ADA, Cl'-OH- and nor-Cl'-(+)-EHNA had comparable inhibitory activity that was 1 order of magnitude lower than that of (+)-EHNA. Potency was reduced further in nor-Cl' derivatives.

  DOI：

  10.1021/jm00100a025