乙基多西他赛 | 154044-47-0

• 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
• 中文名称: 乙基多西他赛
• 英文名称: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,9,12-trihydroxy-15-[(2R,3S)-2-hydroxy-3-(2-methylbutan-2-yloxycarbonylamino)-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: 154044-47-0
• 化学式: C₄₄H₅₅NO₁₄
• 分子量: 821.919
• InChiKey: MQCPMAHSFASPOM-BGKJQISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  59
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  224
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2-甲基-2-丁醇 在 吡啶 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 14.0h， 生成 乙基多西他赛
  参考文献：
  名称：

  Design, synthesis and cytotoxicity of novel 3′-N-alkoxycarbonyl docetaxel analogs

  摘要：

  By-product 9a exhibited potent cytotoxicity against both SK-OV-3 and A549 cell lines. The structure of 9a was characterized using 1D and 2D NMR experiments and confirmed by synthesis to afford a diastereomeric mixture (16a) that was identical to 9a, as well as a pair of diastereomers (R)-16b and (S)-16c. The preliminary SAR study demonstrated that analogs with an (R)-configuration were slightly more potent than analogs with an (S)-configuration. In addition, alpha, alpha-gem-dimethyl analogs 16g-i were the most potent analogs in this series, exhibiting similar potency to docetaxel and greater potency than Taxol against the SK-OV-3 cell line. For the A549 cell line, analogs 16g-i were more potent (>65-fold) than both docetaxel and Taxol. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.007

文献信息

• Design, synthesis and cytotoxicity of novel 3′-N-alkoxycarbonyl docetaxel analogs
  作者：Jun Chang、Xiao-Dong Hao、Yun-Peng Hao、Hong-Fu Lu、Jian-Ming Yu、Xun Sun

  DOI：10.1016/j.bmcl.2013.10.007

  日期：2013.12

  By-product 9a exhibited potent cytotoxicity against both SK-OV-3 and A549 cell lines. The structure of 9a was characterized using 1D and 2D NMR experiments and confirmed by synthesis to afford a diastereomeric mixture (16a) that was identical to 9a, as well as a pair of diastereomers (R)-16b and (S)-16c. The preliminary SAR study demonstrated that analogs with an (R)-configuration were slightly more potent than analogs with an (S)-configuration. In addition, alpha, alpha-gem-dimethyl analogs 16g-i were the most potent analogs in this series, exhibiting similar potency to docetaxel and greater potency than Taxol against the SK-OV-3 cell line. For the A549 cell line, analogs 16g-i were more potent (>65-fold) than both docetaxel and Taxol. (C) 2013 Elsevier Ltd. All rights reserved.