((2R,3R,4S,5R)-3-(benzoyloxy)-4-fluoro-5-(7H-purin-7-yl)tetrahydrofuran-2-yl)methyl benzoate | 132723-15-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: ((2R,3R,4S,5R)-3-(benzoyloxy)-4-fluoro-5-(7H-purin-7-yl)tetrahydrofuran-2-yl)methyl benzoate
• CAS: 132723-15-0
• 化学式: C₂₄H₁₉FN₄O₅
• 分子量: 462.437
• InChiKey: RPOVSDHJOMZESS-XAPVIXHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  105.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  2-脱氧-2-氟-1,3,5-三苯甲酰基-alpha-D-阿拉伯呋喃糖 在 氢溴酸 、 N,O-双(三甲基硅烷基)三氟乙酰胺 、 溶剂黄146 作用下， 反应 1.25h， 生成 ((2R,3R,4S,5R)-3-(benzoyloxy)-4-fluoro-5-(7H-purin-7-yl)tetrahydrofuran-2-yl)methyl benzoate
  参考文献：
  名称：

  Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs

  摘要：

  Selected acid-stable (2'-fluoro-2',3'-dideoxyarabinofuranosyl)adenine nucleosides containing methyl groups and other lipophilic functions at various positions in the adenine ring were prepared and evaluated as anti-HIV agents. The N6-methyl (1f), N6-benzoyl (1g), and 6-chloro (li) analogues had modest activity, giving 30-50% protection to ATH8 cells infected with HIV. 2-Methyl (1d), 8-methyl (1h), and 2,N6-dimethyl (1e) substitution, as well as N1-oxide (21) formation, abolished the activity of the parent compound (1a). Several of these compounds, originally designed as agents for treating HIV in the central nervous system, were further investigated as substrates for adenosine deaminase (ADA). Kinetic experiments showed that ADA catalyzed the formation of the anti-HIV active inosine compound 1b from the N6-methyl analogue 1f in a quantitative manner. The anti-HIV activity of 1f and 1i was abolished when the ADA inhibitor, 2'-deoxycoformycin, was added to the test mixture. In contrast, the activity of 1f was significantly enhanced when ADA was added to the test system. These data indicate that 1f and 1i are prodrug forms of 1b in systems containing ADA.

  DOI：

  10.1021/jm00109a018