[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-6-benzyl-1,9,12-trihydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-azatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate | 194720-17-7

• 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-acetyloxy-6-benzyl-1,9,12-trihydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-azatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 194720-17-7
• 化学式: C₅₀H₆₀N₂O₁₃
• 分子量: 897.032
• InChiKey: LLZAMICENVRMED-RJZLYNIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  65
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  219
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-6-benzyl-1,9,12-trihydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-azatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以61%的产率得到[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,9,12-trihydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-azatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of D-Ring-Modified Taxanes:¹  5(20)-Azadocetaxel Analogs

  摘要：

  Two 5(20)-aza analogs of docetaxel, N-20-benzyl-5(20)-azadocetaxel (5) and 5(20)-azadocetaxel (6), have been synthesized from 10-deacetylbaccatin III, The key steps of this synthesis involved the direct introduction of a C-5 leaving group while ring opening and the intramolecular nucleophilic attack of the C-20 amino group at C-5. Both compounds were inactive on the in vitro cytotoxic assay, and only the azadocetaxel 6 retains an antitubulin activity, but 16 times less than docetaxel.

  DOI：

  10.1021/jo9706842
• 作为产物：
  描述：

  (1S,5S,6R,7S,10R,12S,13S,15R)-9-benzyl-7-hydroxy-13,17,20,20-tetramethyl-12,15-bis(triethylsilyloxy)-2,4-dioxa-9-azapentacyclo[14.3.1.01,5.06,13.07,10]icos-16-ene-3,14,18-trione 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 9.17h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-6-benzyl-1,9,12-trihydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-azatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of D-Ring-Modified Taxanes:¹  5(20)-Azadocetaxel Analogs

  摘要：

  Two 5(20)-aza analogs of docetaxel, N-20-benzyl-5(20)-azadocetaxel (5) and 5(20)-azadocetaxel (6), have been synthesized from 10-deacetylbaccatin III, The key steps of this synthesis involved the direct introduction of a C-5 leaving group while ring opening and the intramolecular nucleophilic attack of the C-20 amino group at C-5. Both compounds were inactive on the in vitro cytotoxic assay, and only the azadocetaxel 6 retains an antitubulin activity, but 16 times less than docetaxel.

  DOI：

  10.1021/jo9706842