9-(2-bromo-2,3-dideoxy-β-D-erythro-pentofuranosyl)adenine | 115941-55-4

• 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-(2-bromo-2,3-dideoxy-β-D-erythro-pentofuranosyl)adenine
• 英文别名: Adenosine, 2'-bromo-2',3'-dideoxy-；[(2S,4R,5R)-5-(6-aminopurin-9-yl)-4-bromooxolan-2-yl]methanol
• CAS: 115941-55-4
• 化学式: C₁₀H₁₂BrN₅O₂
• 分子量: 314.142
• InChiKey: FPZFSLXDWDTIOO-BAJZRUMYSA-N

物化性质

• 沸点：
  585.9±60.0 °C(Predicted)
• 密度：
  2.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  9-(2-O-mesyl-3-deoxy-β-D-erythro-pentofuranosyl)adenine 在 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以35%的产率得到9-(2-bromo-2,3-dideoxy-β-D-erythro-pentofuranosyl)adenine
  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