EP杂质R2,3-二氢三尖杉宁碱 | 158948-96-0

• 中文名称: EP杂质R2,3-二氢三尖杉宁碱
• 英文名称: N-debenzoyl-N-((S)-2-methylbutanoyl)paclitaxel
• 英文别名: Taxol E；[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[[(2S)-2-methylbutanoyl]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] benzoate
• CAS: 158948-96-0
• 化学式: C₄₅H₅₅NO₁₄
• 分子量: 833.93
• InChiKey: OKEKLOJNCOIPIT-RLNDXAGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  60.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  221.29
• 氢给体数：
  4.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  EP杂质R2,3-二氢三尖杉宁碱 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (S)-(+)-2-甲基丁酸
  参考文献：
  名称：

  Synthesis, isolation, stereostructure and cytotoxicity of paclitaxel analogs from cephalomannine

  摘要：

  Four paclitaxel derivatives were afforded by preparative HPLC separation of two pairs of diastereoisomers, which were obtained by catalytic hydrogenation and epoxidation of the C-13 side-chain double bond of cephalomannine, a naturally occurring paclitaxel analog. The four paclitaxel derivatives were analyzed using NMR, CD spectroscopy, and side-chain hydrolysis in order to measure their optical rotations and GC characteristics. In this way, the stereoconfigurations of the products were determined. Evaluation of the compounds' activity indicated that they had differing cytotoxic activities: compound 5 had superior activity in BCG-823 tumor cells compared to paclitaxel, while compound 7 had superior activity in HCT-8 and A549 tumor cells compared to paclitaxel. These results indicate that the stereoconfiguration of the paclitaxel N-acyl side chain has a significant impact on its activity. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2013.07.011
• 作为产物：
  描述：

  三尖杉宁碱 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以85 mg的产率得到EP杂质R2,3-二氢三尖杉宁碱
  参考文献：
  名称：

  Synthesis, isolation, stereostructure and cytotoxicity of paclitaxel analogs from cephalomannine

  摘要：

  Four paclitaxel derivatives were afforded by preparative HPLC separation of two pairs of diastereoisomers, which were obtained by catalytic hydrogenation and epoxidation of the C-13 side-chain double bond of cephalomannine, a naturally occurring paclitaxel analog. The four paclitaxel derivatives were analyzed using NMR, CD spectroscopy, and side-chain hydrolysis in order to measure their optical rotations and GC characteristics. In this way, the stereoconfigurations of the products were determined. Evaluation of the compounds' activity indicated that they had differing cytotoxic activities: compound 5 had superior activity in BCG-823 tumor cells compared to paclitaxel, while compound 7 had superior activity in HCT-8 and A549 tumor cells compared to paclitaxel. These results indicate that the stereoconfiguration of the paclitaxel N-acyl side chain has a significant impact on its activity. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2013.07.011