2'-O-(tert-butoxycarbonyl)paclitaxel | 159500-53-5

• 英文名称: 2'-O-(tert-butoxycarbonyl)paclitaxel
• 英文别名: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-[(2-methylpropan-2-yl)oxycarbonyloxy]-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 159500-53-5
• 化学式: C₅₂H₅₉NO₁₆
• 分子量: 954.038
• InChiKey: KEGOLMRYAZHXJA-XPYIIJPASA-N

物化性质

• 沸点：
  977.8±65.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  69
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  237
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2'-O-(tert-butoxycarbonyl)paclitaxel 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成 2',N-di-O-(tert-butoxycarbonyl)-7-O-(triethylsilyl)paclitaxel
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2-Acyl Analogues of Paclitaxel (Taxol)

  摘要：

  The anticancer drug paclitaxel (Taxol) has been converted to a large number of 2-debenzoyl-2-aroyl derivatives by three different methods. The bioactivities of the resulting analogues were determined in both tubulin polymerization and cytotoxicity assays, and several analogues with enhanced activity as compared with paclitaxel were discovered. Correlation of cytotoxicity in three cell lines with tubulin polymerization activity showed reasonable agreement. Among the cell lines examined, the closest correlation with antitubulin activity was observed with a human ovarian carcinoma cell line.

  DOI：

  10.1021/jm980229d
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 紫杉醇 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以99.6%的产率得到2'-O-(tert-butoxycarbonyl)paclitaxel
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2-Acyl Analogues of Paclitaxel (Taxol)

  摘要：

  The anticancer drug paclitaxel (Taxol) has been converted to a large number of 2-debenzoyl-2-aroyl derivatives by three different methods. The bioactivities of the resulting analogues were determined in both tubulin polymerization and cytotoxicity assays, and several analogues with enhanced activity as compared with paclitaxel were discovered. Correlation of cytotoxicity in three cell lines with tubulin polymerization activity showed reasonable agreement. Among the cell lines examined, the closest correlation with antitubulin activity was observed with a human ovarian carcinoma cell line.

  DOI：

  10.1021/jm980229d