2-O-debenzoyl-2-O-(3-hydroxybenzoyl)paclitaxel

• 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: 2-O-debenzoyl-2-O-(3-hydroxybenzoyl)paclitaxel
• 英文别名: 2-m-Hydroxy(benzoyl) Paclitaxel；[(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] 3-hydroxybenzoate
• 化学式: C₄₇H₅₁NO₁₅
• 分子量: 869.92
• InChiKey: YTVVLBOPTWJFCT-MZXODVADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  63
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  242
• 氢给体数：
  5
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  紫杉醇 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 乙醇 、 potassium tert-butylate 、 氟化氢吡啶 、 N,N'-二环己基碳二亚胺 、 环己烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.5h， 生成 2-O-debenzoyl-2-O-(3-hydroxybenzoyl)paclitaxel
  参考文献：
  名称：

  Preparation of Phenolic Paclitaxel Metabolites

  摘要：

  The synthesis and biological evaluation of the two known phenolic metabolites of paclitaxel are described. The C3'-phenolic metabolite 2 of paclitaxel was prepared from 7-(triethylsilyl)-baccatin III (8) and enantioenriched N-benzoyl-2-azetidinone 7. The C2-phenolic metabolite 3 was synthesized from paclitaxel (1a) via selective C2 debenzoylation and reacylation.

  DOI：

  10.1021/jm960142x

文献信息

• Preparation of Phenolic Paclitaxel Metabolites
  作者：Haeil Park、Michael Hepperle、Thomas C. Boge、Richard H. Himes、Gunda I. Georg

  DOI：10.1021/jm960142x

  日期：1996.1.1

  The synthesis and biological evaluation of the two known phenolic metabolites of paclitaxel are described. The C3'-phenolic metabolite 2 of paclitaxel was prepared from 7-(triethylsilyl)-baccatin III (8) and enantioenriched N-benzoyl-2-azetidinone 7. The C2-phenolic metabolite 3 was synthesized from paclitaxel (1a) via selective C2 debenzoylation and reacylation.
• 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.