5-[(E)-2-bromovinyl]-1-[(2R,4S,5R)-4-methoxy-5-[(8-methyl-2-oxo-4H-1,3,2$l^{5}-benzodioxaphosphinin-2-yl)oxymethyl]tetrahydrofuran-2-yl]pyrimidine-2,4-dione | 376393-40-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 5-[(E)-2-bromovinyl]-1-[(2R,4S,5R)-4-methoxy-5-[(8-methyl-2-oxo-4H-1,3,2$l^{5}-benzodioxaphosphinin-2-yl)oxymethyl]tetrahydrofuran-2-yl]pyrimidine-2,4-dione
• 英文别名: 5-[(E)-2-bromoethenyl]-1-[(2R,4S,5R)-4-methoxy-5-[(8-methyl-2-oxo-4H-1,3,2λ5-benzodioxaphosphinin-2-yl)oxymethyl]oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 376393-40-7
• 化学式: C₂₀H₂₂BrN₂O₈P
• 分子量: 529.281
• InChiKey: RWTOAHUDQIAVMJ-DCVBPICBSA-N

物化性质

• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-[(E)-2-bromovinyl]-1-[(2R,4S,5R)-4-methoxy-5-[(8-methyl-2-oxo-4H-1,3,2$l^{5}-benzodioxaphosphinin-2-yl)oxymethyl]tetrahydrofuran-2-yl]pyrimidine-2,4-dione 在 phosphate buffer 作用下， 反应 8.0h， 生成
  参考文献：
  名称：

  SYNTHESIS, HYDROLYSIS AND ANTI-EBV ACTIVITY OF A SERIES OF 3′-MODIFIEDcycloSal-BVDUMP PRONUCLEOTIDES

  摘要：

  A series of cycloSal-BVDUMP phosphate triesters has been prepared. The prototype compound was 3-methyl-cycloSal-BVDUMP 2. Furthermore, a series of 3'-O-acyl-modified derivatives having carboxylic acids with different lipophilicity or a L-configurated alpha -amino acid (phenylalanine) was prepared. The hydrolysis properties in phosphate buffer PBS as well as in PBS containing pig liver esterase (PLE) will be described. Finally, the biological activity against EBV has been determined.

  DOI：

  10.1081/ncn-100002301
• 作为产物：
  描述：

  溴夫定 在 吡啶 、 叔丁基过氧化氢 、 四丁基氟化铵 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 22.25h， 生成 5-[(E)-2-bromovinyl]-1-[(2R,4S,5R)-4-methoxy-5-[(8-methyl-2-oxo-4H-1,3,2$l^{5}-benzodioxaphosphinin-2-yl)oxymethyl]tetrahydrofuran-2-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  SYNTHESIS, HYDROLYSIS AND ANTI-EBV ACTIVITY OF A SERIES OF 3′-MODIFIEDcycloSal-BVDUMP PRONUCLEOTIDES

  摘要：

  A series of cycloSal-BVDUMP phosphate triesters has been prepared. The prototype compound was 3-methyl-cycloSal-BVDUMP 2. Furthermore, a series of 3'-O-acyl-modified derivatives having carboxylic acids with different lipophilicity or a L-configurated alpha -amino acid (phenylalanine) was prepared. The hydrolysis properties in phosphate buffer PBS as well as in PBS containing pig liver esterase (PLE) will be described. Finally, the biological activity against EBV has been determined.

  DOI：

  10.1081/ncn-100002301

文献信息

• SYNTHESIS, HYDROLYSIS AND ANTI-EBV ACTIVITY OF A SERIES OF 3′-MODIFIED<i>cyclo</i>Sal-BVDUMP PRONUCLEOTIDES
  作者：C. Meier、A. Lomp、A. Meerbach、P. Wutzler

  DOI：10.1081/ncn-100002301

  日期：2001.3.31

  A series of cycloSal-BVDUMP phosphate triesters has been prepared. The prototype compound was 3-methyl-cycloSal-BVDUMP 2. Furthermore, a series of 3'-O-acyl-modified derivatives having carboxylic acids with different lipophilicity or a L-configurated alpha -amino acid (phenylalanine) was prepared. The hydrolysis properties in phosphate buffer PBS as well as in PBS containing pig liver esterase (PLE) will be described. Finally, the biological activity against EBV has been determined.