2-{[(2S,5R)-5-(6-Amino-purin-9-yl)-2,5-dihydro-furan-2-ylmethoxy]-phenoxy-phosphorylamino}-propionic acid benzyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-{[(2S,5R)-5-(6-Amino-purin-9-yl)-2,5-dihydro-furan-2-ylmethoxy]-phenoxy-phosphorylamino}-propionic acid benzyl ester
• 英文别名: d4A Benzyl Phosphate Deriv.；benzyl 2-[[[(2S,5R)-5-(6-aminopurin-9-yl)-2,5-dihydrofuran-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate
• 化学式: C₂₆H₂₇N₆O₆P
• 分子量: 550.511
• InChiKey: OJRXJKPOXXIDMV-OAXBRQIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  153
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  腺苷 在 Mattock's bromide 、 叔丁基氯化镁 、 铜 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 2-{[(2S,5R)-5-(6-Amino-purin-9-yl)-2,5-dihydro-furan-2-ylmethoxy]-phenoxy-phosphorylamino}-propionic acid benzyl ester
  参考文献：
  名称：

  Phosphoramidate derivatives of 2′,3′-didehydro-2′,3′-dideoxyadenosine [d4A] have markedly improved anti-HIV potency and selectivity

  摘要：

  New 5'-phosphate derivatives of the nucleoside analogue d4A were prepared as potential membrane-soluble prodrugs of the free nucleotide. The anti-viral potency and selectivity of the derivatives is markedly increased by comparison to the parent nucleoside analogue. The new analogues show particular promise for further pre-clinical development. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00433-7

文献信息

• Phosphoramidate derivatives of 2′,3′-didehydro-2′,3′-dideoxyadenosine [d4A] have markedly improved anti-HIV potency and selectivity
  作者：Christopher McGuigan、Orson M. Wedgwood、Erik De Clercq、Jan Balzarini

  DOI：10.1016/0960-894x(96)00433-7

  日期：1996.10

  New 5'-phosphate derivatives of the nucleoside analogue d4A were prepared as potential membrane-soluble prodrugs of the free nucleotide. The anti-viral potency and selectivity of the derivatives is markedly increased by comparison to the parent nucleoside analogue. The new analogues show particular promise for further pre-clinical development. Copyright (C) 1996 Elsevier Science Ltd