(Z)-3-iodo-N-methylbut-2-enamide | 1221589-78-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-3-iodo-N-methylbut-2-enamide
• CAS: 1221589-78-1
• 化学式: C₅H₈INO
• 分子量: 225.029
• InChiKey: MOMCSFFZHZIGGH-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,6-二氯-5-甲氧基-1,3-苯硼酸频哪醇酯 、 (Z)-3-iodo-N-methylbut-2-enamide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 3.75h， 生成 (Z)-3-[2,4-dichloro-3-methoxy-5-[(Z)-4-(methylamino)-4-oxobut-2-en-2-yl]phenyl]-N-methylbut-2-enamide
  参考文献：
  名称：

  Chemistry and Biology of Deoxynyboquinone, a Potent Inducer of Cancer Cell Death

  摘要：

  Deoxynyboquinone (DNQ) is a potent antineoplastic agent with an unknown mechanism of action. Here we describe a facile synthetic route to this anthraquinone, and we use this material to determine the mechanism by which DNQ induces death in cancer cells. DNQ was synthesized in seven linear steps through a route employing three palladium-mediated coupling reactions. Experiments performed on cancer cells grown in hypoxia and normoxia strongly suggest that DNQ undergoes bioreduction to its semiquinone, which then is re-oxidized by molecular oxygen, forming superoxide that induces cell death. Furthermore, global transcript profiling of cells treated with DNQ shows elevation of transcripts related to oxidative stress, a result confirmed at the protein level by Western blotting. In contrast to most other antineoplastic agents that generate reactive oxygen species (ROS), DNQ potently induces death of cancer cells in culture, with IC50 values between 16 and 210 nM. In addition, unlike the experimental therapeutic elesclomol, DNQ is still able to induce cancer cell death under hypoxic conditions. This mechanistic understanding of DNQ will allow for a more comprehensive evaluation of the potential of direct ROS generation as an anticancer strategy, and DNQ itself has potential as a novel anticancer agent.

  DOI：

  10.1021/ja100610m
• 作为产物：
  描述：

  N-Methyltetrolamid 在 溶剂黄146 、 sodium iodide 作用下， 反应 8.0h， 以96%的产率得到(Z)-3-iodo-N-methylbut-2-enamide
  参考文献：
  名称：

  Chemistry and Biology of Deoxynyboquinone, a Potent Inducer of Cancer Cell Death

  摘要：

  Deoxynyboquinone (DNQ) is a potent antineoplastic agent with an unknown mechanism of action. Here we describe a facile synthetic route to this anthraquinone, and we use this material to determine the mechanism by which DNQ induces death in cancer cells. DNQ was synthesized in seven linear steps through a route employing three palladium-mediated coupling reactions. Experiments performed on cancer cells grown in hypoxia and normoxia strongly suggest that DNQ undergoes bioreduction to its semiquinone, which then is re-oxidized by molecular oxygen, forming superoxide that induces cell death. Furthermore, global transcript profiling of cells treated with DNQ shows elevation of transcripts related to oxidative stress, a result confirmed at the protein level by Western blotting. In contrast to most other antineoplastic agents that generate reactive oxygen species (ROS), DNQ potently induces death of cancer cells in culture, with IC50 values between 16 and 210 nM. In addition, unlike the experimental therapeutic elesclomol, DNQ is still able to induce cancer cell death under hypoxic conditions. This mechanistic understanding of DNQ will allow for a more comprehensive evaluation of the potential of direct ROS generation as an anticancer strategy, and DNQ itself has potential as a novel anticancer agent.

  DOI：

  10.1021/ja100610m