2-fluoro-9-(3-O-acetyl-2,5-dideoxy-α-D-erythropentofuranosyl)adenine | 675127-82-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 2-fluoro-9-(3-O-acetyl-2,5-dideoxy-α-D-erythropentofuranosyl)adenine
• CAS: 675127-82-9
• 化学式: C₁₂H₁₄FN₅O₃
• 分子量: 295.273
• InChiKey: AAQMAAVSDAXPBO-DTLFHODZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105.15
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-fluoro-9-(3-O-acetyl-2,5-dideoxy-α-D-erythropentofuranosyl)adenine 、 在 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 2-acetamido-N⁶-acetyl-9-(3-O-benzyl-2,5-dideoxy-α-D-erythropentofuranosyl)adenine 、 2-acetamido-N⁶-acetyl-9-(3-O-benzyl-2,5-dideoxy-α-D-erythropentofuranosyl)adenine
  参考文献：
  名称：

  Synthesis of 2‘,5‘-Dideoxy-2-fluoroadenosine and 2‘,5‘-Dideoxy-2,5‘-difluoroadenosine:  Potent P-Site Inhibitors of Adenylyl Cyclase

  摘要：

  Glycosylation of 2-fluoroadenine with the appropriate protected thioglycoside derivatives, followed by deprotection and anomer separation, produced the alpha- and beta-anomers of 2',5'-dideoxy-2-fluoroadenosine (1), 2',5'-dideoxy-2,5'-difluoroadenosine (2), and 2'-deoxy-2-fluoroadenosine (3). These were examined as P-site inhibitors of adenylyl cyclase. The presence of fluorine on the purine ring increased potency of inhibition, and the most potent compound, beta-2',5'-dideoxy-2-fluoroadenosine (1b), was 3 times more potent than beta-2',5'-dideoxyadenosine.

  DOI：

  10.1021/jm0303599
• 作为产物：
  描述：

  methyl 2,5-dideoxy-α,β-D-erythropentofuranoside 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 四丁基碘化铵 、 zinc(II) iodide 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 45.0h， 生成 2-fluoro-9-(3-O-acetyl-2,5-dideoxy-α-D-erythropentofuranosyl)adenine
  参考文献：
  名称：

  Synthesis of 2‘,5‘-Dideoxy-2-fluoroadenosine and 2‘,5‘-Dideoxy-2,5‘-difluoroadenosine:  Potent P-Site Inhibitors of Adenylyl Cyclase

  摘要：

  Glycosylation of 2-fluoroadenine with the appropriate protected thioglycoside derivatives, followed by deprotection and anomer separation, produced the alpha- and beta-anomers of 2',5'-dideoxy-2-fluoroadenosine (1), 2',5'-dideoxy-2,5'-difluoroadenosine (2), and 2'-deoxy-2-fluoroadenosine (3). These were examined as P-site inhibitors of adenylyl cyclase. The presence of fluorine on the purine ring increased potency of inhibition, and the most potent compound, beta-2',5'-dideoxy-2-fluoroadenosine (1b), was 3 times more potent than beta-2',5'-dideoxyadenosine.

  DOI：

  10.1021/jm0303599