3,4-dihydroxy-N-(adamantane-2-spiro-3'-1',2',5'-trioxaspiro[5.5]undecan-9'-yl)benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-dihydroxy-N-(adamantane-2-spiro-3'-1',2',5'-trioxaspiro[5.5]undecan-9'-yl)benzamide
• 化学式: C₂₄H₃₁NO₆
• 分子量: 429.513
• InChiKey: FMHSCNXAYIWCIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  原儿茶酸 、 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以43%的产率得到3,4-dihydroxy-N-(adamantane-2-spiro-3'-1',2',5'-trioxaspiro[5.5]undecan-9'-yl)benzamide
  参考文献：
  名称：

  Antitumor activity of endoperoxide-iron chelator conjugates―design, synthesis and biological evaluation

  摘要：

  The effort to pursue effective anti-cancer drugs with novel mechanism of action has been continued for decades. As an antimalarial agent, artemisinin is well-known for its endoperoxide moiety, which is activated by the cellular iron. Meanwhile, the anti-cancer activity of artemisinin is recognized and reported. Herein, we report on the design, synthesis and evaluation of a series of endoperoxide and iron chelating moiety conjugates. Our study demonstrated that the endoperoxide-quinoline conjugates displayed effective antiproliferative capability and good selectivity against certain cancer cells, while both hydroxamate and catechol-endoperoxide conjugates shown no significant inhibitory activity. Preliminary mechanism investigation suggested that the antiproliferative activity of these conjugates is related to the endoperoxide moiety as well as their iron-chelating ability. These compounds are expected to be used as prototype for further development of selective anti-cancer drug candidate. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.040

文献信息

• Antitumor activity of endoperoxide-iron chelator conjugates―design, synthesis and biological evaluation
  作者：Xing Yan、Yang Yu、Peng Ji、Hui He、Chunhua Qiao

  DOI：10.1016/j.ejmech.2015.07.040

  日期：2015.9

  The effort to pursue effective anti-cancer drugs with novel mechanism of action has been continued for decades. As an antimalarial agent, artemisinin is well-known for its endoperoxide moiety, which is activated by the cellular iron. Meanwhile, the anti-cancer activity of artemisinin is recognized and reported. Herein, we report on the design, synthesis and evaluation of a series of endoperoxide and iron chelating moiety conjugates. Our study demonstrated that the endoperoxide-quinoline conjugates displayed effective antiproliferative capability and good selectivity against certain cancer cells, while both hydroxamate and catechol-endoperoxide conjugates shown no significant inhibitory activity. Preliminary mechanism investigation suggested that the antiproliferative activity of these conjugates is related to the endoperoxide moiety as well as their iron-chelating ability. These compounds are expected to be used as prototype for further development of selective anti-cancer drug candidate. (C) 2015 Elsevier Masson SAS. All rights reserved.