(14S)-14β-(2-oxo-2,3-dihydrobenzofuran-5-ylamino)methylepitriptolide | 1563176-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (14S)-14β-(2-oxo-2,3-dihydrobenzofuran-5-ylamino)methylepitriptolide
• 英文别名: (1S,2S,4S,5S,7S,8S,9R,11S,13S)-8-hydroxy-1-methyl-8-[[(2-oxo-3H-1-benzofuran-5-yl)amino]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: 1563176-20-4
• 化学式: C₂₉H₃₁NO₈
• 分子量: 521.567
• InChiKey: OSNORKUEAQJLCO-ACWNRLHJSA-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：
  0.66
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (14S)-14β-(hydroxymethyl)epitriptolide 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 三氯异氰尿酸 、 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (14S)-14β-(2-oxo-2,3-dihydrobenzofuran-5-ylamino)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

文献信息

• Design, synthesis and anticancer activity evaluation of novel C14 heterocycle substituted epi-triptolide
  作者：Hongtao Xu、Huanyu Tang、Huijin Feng、Yuanchao Li

  DOI：10.1016/j.ejmech.2013.11.044

  日期：2014.2

  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.