9-(5-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)guanine | 115913-75-2

• 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: 9-(5-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)guanine
• 英文别名: [(2R,3R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methyl benzoate
• CAS: 115913-75-2
• 化学式: C₁₇H₁₇N₅O₅
• 分子量: 371.352
• InChiKey: WKKWWJHUSSVUAH-IJLUTSLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.21
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  145.35
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  9-(5-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)guanine 生成 5'-O-benzoyl-3'-azido-2',3'-dideoxyguanosine
  参考文献：
  名称：

  HERDEWIJN, PIET;BALZARINI, JAN;BADA, MASANORI;PAUWELS, RUDI;VAN, AERSCHOT+, J. MED. CHEM., 31,(1988) N 10, C. 2040-2048

  摘要：

  DOI：
• 作为产物：
  描述：

  鸟苷 在 4-二甲氨基吡啶 、 氨 、 三乙基硼氢化锂 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 65.0h， 生成 9-(5-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)guanine
  参考文献：
  名称：

  Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides

  摘要：

  A series of base-modified pyrimidine 3'-azido-2',3'-dideoxynucleosides and 3'-substituted purine and pyrimidine 2',3'-dideoxynucleosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. The following pyrimidine derivatives emerged as the most potent and/or selective inhibitors of HIV-induced cytopathogenicity (in order of decreasing selectivity: 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AzddUrd), 3'-azido-2',3'-dideoxy-5-methylcytidine (AzddMeCyd), 3'-fluoro-ddUrd (FddUrd), 3'-fluoro-ddThd (FddThd), the N4-hydroxylated derivative of AzddMeCyd and the N4-methylated derivative of AzddMeCyd. Among the purine 2',3'-dideoxynucleosides, 3'-azido-2',3'-dideoxyguanosine (AzddGuo), 3'-fluoro-ddGuo (FddGuo), and 3'-fluoro-2,6-diaminopurine 2',3'-dideoxynucleoside (FddDAPR) were the most selective inhibitors of HIV replication.

  DOI：

  10.1021/jm00118a033