10-[(2-nitrophenyl)acetyl]-10-deacetylpaclitaxel

• 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: 10-[(2-nitrophenyl)acetyl]-10-deacetylpaclitaxel
• 英文别名: [(1S,2S,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-(3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-12-[2-(2-nitrophenyl)acetyl]oxy-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• 化学式: C₅₃H₅₄N₂O₁₆
• 分子量: 975.016
• InChiKey: BFVNEYZEWBLNDJ-PNQZAKAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  71
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  267
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  10-[(2-nitrophenyl)acetyl]-10-deacetylpaclitaxel 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 8.0h， 以63%的产率得到10-[(2-aminophenyl)acetyl]-10-deacetylpaclitaxel
  参考文献：
  名称：

  Synthesis and Evaluation of Some 10-Mono- and 2',10-Diesters of 10-Deacetylpaclitaxel

  摘要：

  10-Deacetylpaclitaxel, isolated from the bark of Taxus brevifolia, was converted into paclitaxel in one composite step (trimethylsilylation, acetylation, and desilylation) and in an overall yield of 80-85%. A series of 10-monoesters of 10-deacetylpaclitaxel are prepared by protection of the 2'- and 7-hydroxyls with a chloroacetyl group, acylation, and deprotection. Depending on the reaction conditions, the 10-monoesters, either exclusively or accompanied by the 2',10-diesters, are formed. The mono- and diesters were evaluated using the L-1210 cell culture assay. The 10-monoesters were comparable to paclitaxel and more active than the corresponding 2',10-diesters. The 10-[(4-methoxyphellyl)acetyl], 10-(2-nitrobenzoyl), and 10-(phenylacetyl) esters were found to be somewhat more active than paclitaxel.

  DOI：

  10.1021/jm00017a026
• 作为产物：
  描述：

  2-硝基苯乙酸 在 4-二甲氨基吡啶 、 硫脲 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 10.0h， 生成 10-[(2-nitrophenyl)acetyl]-10-deacetylpaclitaxel
  参考文献：
  名称：

  Synthesis and Evaluation of Some 10-Mono- and 2',10-Diesters of 10-Deacetylpaclitaxel

  摘要：

  10-Deacetylpaclitaxel, isolated from the bark of Taxus brevifolia, was converted into paclitaxel in one composite step (trimethylsilylation, acetylation, and desilylation) and in an overall yield of 80-85%. A series of 10-monoesters of 10-deacetylpaclitaxel are prepared by protection of the 2'- and 7-hydroxyls with a chloroacetyl group, acylation, and deprotection. Depending on the reaction conditions, the 10-monoesters, either exclusively or accompanied by the 2',10-diesters, are formed. The mono- and diesters were evaluated using the L-1210 cell culture assay. The 10-monoesters were comparable to paclitaxel and more active than the corresponding 2',10-diesters. The 10-[(4-methoxyphellyl)acetyl], 10-(2-nitrobenzoyl), and 10-(phenylacetyl) esters were found to be somewhat more active than paclitaxel.

  DOI：

  10.1021/jm00017a026

文献信息

• Synthesis and Evaluation of Some 10-Mono- and 2',10-Diesters of 10-Deacetylpaclitaxel
  作者：Koppaka V. Rao、Rajendra S. Bhakuni、James Johnson、Ravi Oruganti

  DOI：10.1021/jm00017a026

  日期：1995.8

  10-Deacetylpaclitaxel, isolated from the bark of Taxus brevifolia, was converted into paclitaxel in one composite step (trimethylsilylation, acetylation, and desilylation) and in an overall yield of 80-85%. A series of 10-monoesters of 10-deacetylpaclitaxel are prepared by protection of the 2'- and 7-hydroxyls with a chloroacetyl group, acylation, and deprotection. Depending on the reaction conditions, the 10-monoesters, either exclusively or accompanied by the 2',10-diesters, are formed. The mono- and diesters were evaluated using the L-1210 cell culture assay. The 10-monoesters were comparable to paclitaxel and more active than the corresponding 2',10-diesters. The 10-[(4-methoxyphellyl)acetyl], 10-(2-nitrobenzoyl), and 10-(phenylacetyl) esters were found to be somewhat more active than paclitaxel.