N-de-tert-butoxycarbonyl-7,10-di(2,2,2-trichloroethyloxycarbonyl)-2-debenzoyl-2-(m-fluorobenzoyl)docetaxel | 912271-98-8

• 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: N-de-tert-butoxycarbonyl-7,10-di(2,2,2-trichloroethyloxycarbonyl)-2-debenzoyl-2-(m-fluorobenzoyl)docetaxel
• 英文别名: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-15-[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis(2,2,2-trichloroethoxycarbonyloxy)-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 3-fluorobenzoate
• CAS: 912271-98-8
• 化学式: C₄₄H₄₆Cl₆FNO₁₆
• 分子量: 1076.56
• InChiKey: MGUXVZCHEWVZHT-YXOTWFKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  68
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  243
• 氢给体数：
  3
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  (1,1,1-Trifluoro-2-methylpropan-2-yl) carbonochloridate 、 N-de-tert-butoxycarbonyl-7,10-di(2,2,2-trichloroethyloxycarbonyl)-2-debenzoyl-2-(m-fluorobenzoyl)docetaxel 以 水 、 乙酸乙酯 为溶剂， 以35%的产率得到N-de-tert-butoxycarbonyl-N-[2-(1,1,1-trifluoro-2-methyl)-propyloxycarbonyl]-7,10-di(2,2,2-trichloroethyloxycarbonyl)-2-debenzoyl-2-(m-fluorobenzoyl)docetaxel
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel fluorinated docetaxel analogues

  摘要：

  A series of novel fluorinated docetaxel analogues have been synthesized and evaluated in vitro and in vivo. Incorporated one, two or three fluorine atom(s) either at both meta position on C-2 benzolate and 3'-N-tert-butyloxyl group or only at 3-N-tert-butyloxyl group has resulted in potent analogues which have comparable or superior in vitro and in vivo cytotoxicity to docetaxel. Among them, compounds 14d and 14e have displayed more potent cytotoxicity than docetaxel both in human cancer cell line SK-OV-3 in vitro and in human non-small cell lung cancer A549 xenografts in vivo. Preliminary data show that compound 14a has reduced acute animal toxicity in mice compared with docetaxel. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.04.004
• 作为产物：
  描述：

  7,10-di(2,2,2-trichloroethyloxycarbonyl)-2-debenzoyl-2-(m-fluorobenzoyl)-10-deacetylbaccatin III-13-O-[(4S,5R)-4-phenyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate] 在 甲酸 作用下， 反应 2.0h， 以99%的产率得到N-de-tert-butoxycarbonyl-7,10-di(2,2,2-trichloroethyloxycarbonyl)-2-debenzoyl-2-(m-fluorobenzoyl)docetaxel
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel fluorinated docetaxel analogues

  摘要：

  A series of novel fluorinated docetaxel analogues have been synthesized and evaluated in vitro and in vivo. Incorporated one, two or three fluorine atom(s) either at both meta position on C-2 benzolate and 3'-N-tert-butyloxyl group or only at 3-N-tert-butyloxyl group has resulted in potent analogues which have comparable or superior in vitro and in vivo cytotoxicity to docetaxel. Among them, compounds 14d and 14e have displayed more potent cytotoxicity than docetaxel both in human cancer cell line SK-OV-3 in vitro and in human non-small cell lung cancer A549 xenografts in vivo. Preliminary data show that compound 14a has reduced acute animal toxicity in mice compared with docetaxel. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.04.004