7-succinylpaclitaxel | 146462-53-5

• 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: 7-succinylpaclitaxel
• 英文别名: 7-hemisuccinylpaclitaxel；4-[[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-2-benzoyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-9-yl]oxy]-4-oxobutanoic acid
• CAS: 146462-53-5
• 化学式: C₅₁H₅₅NO₁₇
• 分子量: 953.994
• InChiKey: VKWHFTYOXABIGQ-LAVNIZMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  69
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  265
• 氢给体数：
  4
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  2'-O-(叔-丁基二甲基硅烷基)紫杉醇 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 7-succinylpaclitaxel
  参考文献：
  名称：

  水溶性抗肿瘤化合物

  摘要：

  本发明涉及如式（Ⅰ）所示的水溶性抗肿瘤化合物，本发明还涉及所述化合物的制备方法及其用于制备抗肿瘤药物的用途。通过本发明的修饰方式可以得到水溶性好的稳定的紫杉醇类、喜树碱类等抗肿瘤化合物前药，克服由于溶剂或辅料原因导致的副作用。Drug‑Linker‑FG（I）。

  公开号：

  CN104370862B

文献信息

• Paclitaxel succinate analogs: Anionic and amide introduction as a strategy to impart blood–brain barrier permeability
  作者：Brandon J. Turunen、Haibo Ge、Jariat Oyetunji、Kelly E. Desino、Veena Vasandani、Sarah Güthe、Richard H. Himes、Kenneth L. Audus、Anna Seelig、Gunda I. Georg

  DOI：10.1016/j.bmcl.2008.09.103

  日期：2008.11

  A focused library of TX-67 (C10 hemi-succinate) analogs has been prepared, including C7 regioisomers, esters, amides, and one-carbon homologs. These were prepared to investigate whether the lack of TX-67 interaction with P-glycoprotein (Pgp) is due to the presence of the carboxylic acid moiety and whether this phenomenon was restricted to C10 analogs. Tubulin stabilization ability, cytotoxicity, and Pgp interactions were evaluated. All carboxylic acid analogs and several of the amides had no apparent interactions with Pgp at the concentrations used, whereas the ester variants displayed characteristics of Pgp substrates. Furthermore, it was demonstrated that hydrogen-bonding properties were significant with respect to Pgp interactions. Calculations of logD and cross-sectional areas revealed that these analogs are predicted to partition into the membrane and can compete for Pgp binding sites. The anionic and amide introduction strategy may allow for delivery of paclitaxel into the CNS and may be a potential approach for the delivery of other, structurally complex and lipophilic non-CNS permeable drugs. (C) 2008 Elsevier Ltd. All rights reserved.