(14S)-14β-(4-phenyl-1H-1,2,3-triazol-1-yl)methylepitriptolide | 1563176-00-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (14S)-14β-(4-phenyl-1H-1,2,3-triazol-1-yl)methylepitriptolide
• 英文别名: (1S,2S,4S,5S,7S,8S,9R,11S,13S)-8-hydroxy-1-methyl-8-[(4-phenyltriazol-1-yl)methyl]-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one
• CAS: 1563176-00-0
• 化学式: C₂₉H₃₁N₃O₆
• 分子量: 517.582
• InChiKey: KHEQYEODYBUFEV-HXCPCIJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (14S)-14β-(hydroxymethyl)epitriptolide 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 氯化铵 、 sodium ascorbate 作用下， 以 吡啶 、 甲醇 、 乙二醇甲醚 、 水 、 叔丁醇 为溶剂， 反应 24.5h， 生成 (14S)-14β-(4-phenyl-1H-1,2,3-triazol-1-yl)methylepitriptolide
  参考文献：
  名称：

  Design, synthesis and anticancer activity evaluation of novel C14 heterocycle substituted epi-triptolide

  摘要：

  Two series of novel C14 heterocycle substituted epi-triptolide derivatives as potential anticancer agents were synthesized and tested for their cytotoxicity against SKOV-3 and PC-3 tumor cell lines. The introduction of C14 beta-aryl heterocycle aminomethyl substituent to the leading compound was found to be an effective modification method to retain the potent anticancer activity. Meanwhile, the series of epitriptolide derivatives (21-40) with C14 alpha-hydroxyl group, still retained the natural product's cytotoxicity. This is apparently challenges the classical structure activity relationship of triptolide that considers the C14 beta-hydroxyl group to be essential for its anticancer activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.044