[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-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] 2-methoxybenzoate | 213764-99-9

• 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
• 英文名称: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-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] 2-methoxybenzoate
• CAS: 213764-99-9
• 化学式: C₄₈H₅₃NO₁₅
• 分子量: 883.947
• InChiKey: HEYAFKGXVCOFGR-JBTWBBNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  64
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  231
• 氢给体数：
  4
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  紫杉醇 在 咪唑 、 盐酸 、 甲醇 、 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 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-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] 2-methoxybenzoate
  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.