5'-O-(3-N-Fmoc-aminopropanoyl)-2',3'-didehydro-2',3'-dideoxythymidine | 1289430-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 5'-O-(3-N-Fmoc-aminopropanoyl)-2',3'-didehydro-2',3'-dideoxythymidine
• CAS: 1289430-08-5
• 化学式: C₂₈H₂₇N₃O₇
• 分子量: 517.538
• InChiKey: IVVDXZKMMQTVGK-MHECFPHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  128.72
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5'-O-(3-N-Fmoc-aminopropanoyl)-2',3'-didehydro-2',3'-dideoxythymidine 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以40 mg的产率得到5'-O-(3-aminopropanoyl)-2',3'-didehydro-2',3'-dideoxythymidine
  参考文献：
  名称：

  Synthesis and biological evaluation of fatty acyl ester derivatives of 2′,3′-didehydro-2′,3′-dideoxythymidine

  摘要：

  A number of 5'-O-fatty acyl derivatives of 2',3'-didehydro-2',3'-dideoxythymidine (stavudine, d4T) were synthesized and evaluated for anti-HIV activities against cell-free and cell-associated virus, cellular cytotoxicity, and cellular uptake studies. The conjugates were found to be more potent than d4T. Among these conjugates, 5'-O-12-azidododecanoyl derivative of d4T (2), displaying EC50 = 3.1-22.4 mu M, showed 4- to 9-fold higher activities than d4T against cell-free and cell-associated virus. Cellular uptake studies were conducted on CCRF-CEM cell line using 5(6)-carboxyfluorescein derivatives of d4T attached through beta-alanine (9) or 12-aminododecanoic acid (10) as linkers. The fluorescein-substituted analog of d4T with long chain length (10) showed 12- to 15-fold higher cellular uptake profile than the corresponding analog with short chain length (9). These studies reveal that conjugation of fatty acids to d4T enhances the cellular uptake and anti-HIV activity of stavudine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.070
• 作为产物：
  描述：

  FMOC-beta-丙氨酸 、 司他夫定 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5'-O-(3-N-Fmoc-aminopropanoyl)-2',3'-didehydro-2',3'-dideoxythymidine
  参考文献：
  名称：

  Synthesis and biological evaluation of fatty acyl ester derivatives of 2′,3′-didehydro-2′,3′-dideoxythymidine

  摘要：

  A number of 5'-O-fatty acyl derivatives of 2',3'-didehydro-2',3'-dideoxythymidine (stavudine, d4T) were synthesized and evaluated for anti-HIV activities against cell-free and cell-associated virus, cellular cytotoxicity, and cellular uptake studies. The conjugates were found to be more potent than d4T. Among these conjugates, 5'-O-12-azidododecanoyl derivative of d4T (2), displaying EC50 = 3.1-22.4 mu M, showed 4- to 9-fold higher activities than d4T against cell-free and cell-associated virus. Cellular uptake studies were conducted on CCRF-CEM cell line using 5(6)-carboxyfluorescein derivatives of d4T attached through beta-alanine (9) or 12-aminododecanoic acid (10) as linkers. The fluorescein-substituted analog of d4T with long chain length (10) showed 12- to 15-fold higher cellular uptake profile than the corresponding analog with short chain length (9). These studies reveal that conjugation of fatty acids to d4T enhances the cellular uptake and anti-HIV activity of stavudine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.070