[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-(3,3,3-trichloropropanoyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate | 1053622-25-5

• 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: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-(3,3,3-trichloropropanoyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 1053622-25-5
• 化学式: C₃₄H₃₉Cl₃O₁₂
• 分子量: 746.035
• InChiKey: BSAMOYYWSPISAX-KGLKXFLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  49
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  172
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-(3,3,3-trichloropropanoyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 8.5h， 生成
  参考文献：
  名称：

  Synthesis and anticancer activity of novel quinoline–docetaxel analogues

  摘要：

  A series of novel quinoline-docetaxel analogues (6a-6g, 13a-13g) were designed and synthesized by introducing bioactive quinoline scaffold to C2'-OH of docetaxel. The anticancer activities of these novel analogues were investigated against different human cancer cell lines including Hela, A549, A2780, MCF-7 and two resistant strains A2780-MDR and MCF-7-MDR. The data showed these analogues possessed similar to better cytotoxicity than docetaxel. Compound 6c was found to be the most potent one, and its IC50 value against MCF-7-MDR was 8.8 nM (IC50 of docetaxel was 180 nM). The work indicated that the introduction of quinolyl group in docetaxel could enhance cytotoxicity and reduce drug-resistance. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.091
• 作为产物：
  描述：

  10-脱乙酰基巴卡丁 III 在 乙酸酐 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 0.5h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-(3,3,3-trichloropropanoyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Synthesis and anticancer activity of novel quinoline–docetaxel analogues

  摘要：

  A series of novel quinoline-docetaxel analogues (6a-6g, 13a-13g) were designed and synthesized by introducing bioactive quinoline scaffold to C2'-OH of docetaxel. The anticancer activities of these novel analogues were investigated against different human cancer cell lines including Hela, A549, A2780, MCF-7 and two resistant strains A2780-MDR and MCF-7-MDR. The data showed these analogues possessed similar to better cytotoxicity than docetaxel. Compound 6c was found to be the most potent one, and its IC50 value against MCF-7-MDR was 8.8 nM (IC50 of docetaxel was 180 nM). The work indicated that the introduction of quinolyl group in docetaxel could enhance cytotoxicity and reduce drug-resistance. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.091