7-O-(三乙基硅烷基)-2'-O-叔丁基(二甲基)硅烷基 2-去苯甲酰基紫杉醇 2-戊酸酯 | 1055033-93-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 7-O-(三乙基硅烷基)-2'-O-叔丁基(二甲基)硅烷基 2-去苯甲酰基紫杉醇 2-戊酸酯
• 中文别名: 7-O-(三乙基硅烷基)-2'-O-叔丁基(二甲基)硅烷基2-去苯甲酰基紫杉醇2-戊酸酯；7-O-（三乙基甲硅烷基）-2'-O-叔丁基（二甲基）甲硅烷基-2-脱苯甲酰基紫杉醇-2-戊酸酯
• 英文名称: 7-O-(Triethylsilyl)-2'-O-tert-butyl(dimethyl)silyl 2-Debenzoyl Paclitaxel 2-Pentanoate
• 英文别名: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] pentanoate
• CAS: 1055033-93-6
• 化学式: C₅₇H₈₃NO₁₄Si₂
• 分子量: 1062.46
• InChiKey: WRUFGKOUUYXVIA-XZLAFKNDSA-N

物化性质

• 溶解度：
  可溶于氯仿、二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  9.67
• 重原子数：
  74
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  199
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  7-O-(三乙基硅烷基)-2'-O-叔丁基(二甲基)硅烷基 2-去苯甲酰基紫杉醇 2-戊酸酯 在 盐酸 、 甲醇 作用下， 生成 2-去苯酰基紫杉醇-2-戊烯酸酯
  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：

  紫杉醇 在 咪唑 、 苄基三甲基氢氧化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.08h， 生成 7-O-(三乙基硅烷基)-2'-O-叔丁基(二甲基)硅烷基 2-去苯甲酰基紫杉醇 2-戊酸酯
  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

文献信息

• Synthesis and Biological Evaluation of 2-Acyl Analogues of Paclitaxel (Taxol)
  作者：David G. I. Kingston、Ashok G. Chaudhary、Mahendra D. Chordia、Milind Gharpure、A. A. Leslie Gunatilaka、Paul I. Higgs、John M. Rimoldi、Lakshman Samala、Prakash G. Jagtap、Paraskevi Giannakakou、Yuan Q. Jiang、Chii M. Lin、Ernest Hamel、Byron H. Long、Craig R. Fairchild、Kathy A. Johnston

  DOI：10.1021/jm980229d

  日期：1998.9.1

  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.