2-O-debenzoyl-2',7-bis(O-triethylsilyl)paclitaxel | 156266-04-5

• 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',7-bis(O-triethylsilyl)paclitaxel
• 英文别名: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,2-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl] (2R,3S)-3-benzamido-3-phenyl-2-triethylsilyloxypropanoate
• CAS: 156266-04-5
• 化学式: C₅₂H₇₅NO₁₃Si₂
• 分子量: 978.337
• InChiKey: IRPMIYLKJPGGKV-FQGSOGPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.93
• 重原子数：
  68
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  193
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-O-debenzoyl-2',7-bis(O-triethylsilyl)paclitaxel 在 盐酸 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 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] 4-cyanobenzoate
  参考文献：
  名称：

  Unexpectedly Facile Hydrolysis of the 2-Benzoate Group of Taxol and Syntheses of Analogs with Increased Activities

  摘要：

  DOI：

  10.1021/ja00088a063
• 作为产物：
  描述：

  (2'R,3'S)-2',7-(bis)triethylsilyl taxol 在 红铝 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以12.5 g的产率得到2-O-debenzoyl-2',7-bis(O-triethylsilyl)paclitaxel
  参考文献：
  名称：

  一种紫杉醇衍生物及其制备方法

  摘要：

  本发明公开了一种紫杉醇衍生物及其制备方法,包属于紫杉烷类抗癌药物的制备领域,包括所述紫杉醇衍生物为2‑去苯甲酰基‑2‑惕格酰基紫杉醇,制备方法包括：将紫杉醇和2‑甲基咪唑用N,N‑二甲基甲酰胺溶解，搅拌下滴加三乙基氯硅烷，得到产物I；产物I用四氢呋喃溶解,低温下搅拌滴加红铝溶液，反应完并纯化得到产物II；将惕格酸加入二氯亚砜中回流反应得到惕格酰氯，将产物II溶于二氯甲烷和三乙胺中，低温下搅拌滴加惕格酰氯，得到产物III；将产物III溶于乙腈中，加入盐酸溶液搅拌反应，产物经过柱层析纯化并除去溶剂得到2‑去苯甲酰基‑2‑惕格酰基紫杉醇，本发明的优点在于各步骤收率高，产品纯度好，易分离，可以进行大量制备。

  公开号：

  CN113620911A

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.
• Synthesis and biological activity of A-nor-paclitaxel analogues
  作者：Mahendra D. Chordia、David G.I. Kingston、Ernest Hamel、Chii M. Lin、Byron H. Long、Craig A. Fairchild、Kathy A. Johnston、William C. Rose

  DOI：10.1016/s0968-0896(97)00035-7

  日期：1997.5

  A number of paclitaxel analogues with a 5-membered A-ring (A-nor-paclitaxels, or (15 right-arrow 1)-abeo-paclitaxels) have been prepared in order to determine whether analogues of this class might have improved bioactivity as compared with paclitaxel. Most of the compounds synthesized were less active than paclitaxel, but one analogue was equivalent to paclitaxel in a tubulin-assembly assay, and another analogue was more cytotoxic than paclitaxel in two different cell lines of the NCI screen.