[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-9-[2-(dimethylamino)acetyl]oxy-1,12-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 3-azidobenzoate | 1329497-68-8

• 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-9-[2-(dimethylamino)acetyl]oxy-1,12-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 3-azidobenzoate
• CAS: 1329497-68-8
• 化学式: C₄₇H₅₇N₅O₁₄
• 分子量: 915.995
• InChiKey: UDFQLYGGOGCSPO-HPYSULPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  66
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  239
• 氢给体数：
  4
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  三尖杉宁碱 在 吡啶 、 咪唑 、 氢氟酸 、 苄基三甲基氢氧化铵 、 4-吡咯烷基吡啶 、 一水合肼 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 30.08h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-9-[2-(dimethylamino)acetyl]oxy-1,12-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 3-azidobenzoate
  参考文献：
  名称：

  Effects of C7 substitutions in a high affinity microtubule-binding taxane on antitumor activity and drug transport

  摘要：

  Some C-7 modified analogs of 3, a taxane with high affinity for binding to microtubules, were prepared through multistep transformations. Most of the analogs, bearing less lipophilic C-7 substituents than propionyl in 3, exhibited comparable binding affinities to microtubules but less cytotoxicity against drug-sensitive as well as multidrug-resistant tumor cells overexpressing P-glycoprotein. In addition, these C7 modifications increased P-glycoprotein-mediated drug transport in both directions in a Caco-2 cell assay. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.034

文献信息

• Effects of C7 substitutions in a high affinity microtubule-binding taxane on antitumor activity and drug transport
  作者：Xi Xiao、Ju Wu、Chiara Trigili、Hui Chen、Joseph W.K. Chu、Ying Zhao、Peihua Lu、Li Sheng、Yan Li、Frances J. Sharom、Isabel Barasoain、J. Fernando Diaz、Wei-shuo Fang

  DOI：10.1016/j.bmcl.2011.06.034

  日期：2011.8

  Some C-7 modified analogs of 3, a taxane with high affinity for binding to microtubules, were prepared through multistep transformations. Most of the analogs, bearing less lipophilic C-7 substituents than propionyl in 3, exhibited comparable binding affinities to microtubules but less cytotoxicity against drug-sensitive as well as multidrug-resistant tumor cells overexpressing P-glycoprotein. In addition, these C7 modifications increased P-glycoprotein-mediated drug transport in both directions in a Caco-2 cell assay. (C) 2011 Elsevier Ltd. All rights reserved.