1-(3-Azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-methyl-4-pentafluorophenyloxy-2(1H)-pyrimidinone

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(3-Azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-methyl-4-pentafluorophenyloxy-2(1H)-pyrimidinone
• 英文别名: 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-4-(2,3,4,5,6-pentafluorophenoxy)pyrimidin-2-one；1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-4-(2,3,4,5,6-pentafluorophenoxy)pyrimidin-2-one
• 化学式: C₁₆H₁₂F₅N₅O₄
• 分子量: 433.294
• InChiKey: SWVYMDKRSOKWQO-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.7
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  齐多夫定 在 吡啶 、 水 作用下， 反应 25.75h， 生成 1-(3-Azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-methyl-4-pentafluorophenyloxy-2(1H)-pyrimidinone
  参考文献：
  名称：

  Synthesis and anti-HIV activity of C4-modified pyrimidine nucleosides

  摘要：

  One-pot syntheses provided a series of triazole- and pentafluorophenyloxy-substituted pyrimidine nucleosides. Most of the compounds in the series displayed anti-HIV activities but none as potent as AZT 2. 1-(beta-D-Erythro-pentofuranosyl)-4-pentafluorophenyloxy-2(1H)-pyr imidinone 14 was the most potent and the most selective compound in the series with EC50 = 1.6 microM.

  DOI：

  10.1016/s0014-827x(98)00107-4

文献信息

• Synthesis and anti-HIV activity of C4-modified pyrimidine nucleosides
  作者：Mark P Wallis、Naheed Mahmood、William Fraser

  DOI：10.1016/s0014-827x(98)00107-4

  日期：1999.1

  One-pot syntheses provided a series of triazole- and pentafluorophenyloxy-substituted pyrimidine nucleosides. Most of the compounds in the series displayed anti-HIV activities but none as potent as AZT 2. 1-(beta-D-Erythro-pentofuranosyl)-4-pentafluorophenyloxy-2(1H)-pyr imidinone 14 was the most potent and the most selective compound in the series with EC50 = 1.6 microM.