[(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] furan-2-carboxylate

• 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] furan-2-carboxylate
• 化学式: C₄₅H₄₉NO₁₅
• 分子量: 843.882
• InChiKey: UCLXBYBARUOWKB-MHHARFCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  61
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  234
• 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] furan-2-carboxylate
  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

• Chemical Synthesis and Biological Evaluation of C-2 Taxoids
  作者：K. C. Nicolaou、J. Renaud、P. G. Nantermet、E. A. Couladouros、R. K. Guy、W. Wrasidlo

  DOI：10.1021/ja00114a005

  日期：1995.3

  An efficient, general method for the synthesis of 1,2-hydroxy esters by regioselective nucleophilic opening of 1,2-cyclic carbonate systems has been developed. A reliable and practical route giving access to the taxoid carbonate 2 from the readily available 10-deacetylbaccatin III (13) has been established. Nucleophilic opening of the carbonate 2 with a variety of nucleophiles provided a number of novel C-2 Taxols. Water-soluble taxoid onium salts (e.g., 31e, 31n, 32, and 34b) were also synthesized and studied. A selected number of taxoids were subjected to cytotoxicity and tubulin polymerization assays as well as in vivo studies. The results of these studies are reported herein.
• Nicolaou, Kyriacos Costa; Couladouros, E. A.; Nantermet, P. G., Angewandte Chemie, 1994, vol. 106, # 15/16, p. 1669 - 1671
  作者：Nicolaou, Kyriacos Costa、Couladouros, E. A.、Nantermet, P. G.、Renaud, J.、Guy, Rodney Kiplin、Wrasidlo, Wolfgang

  DOI：——

  日期：——
• 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.