N-Methyltetrolamid | 63798-30-1

• 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: N-Methyltetrolamid
• 英文别名: N-Methyl-2-butynamide；N-methylbut-2-ynamide
• CAS: 63798-30-1
• 化学式: C₅H₇NO
• 分子量: 97.1167
• InChiKey: NFKDOZIFRBUOCG-UHFFFAOYSA-N

物化性质

• 熔点：
  61.5-63.5 °C
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  7
• 可旋转键数：
  0
• 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：

  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
• 作为产物：
  描述：

  2-丁炔酸乙酯 、 甲胺 以 甲醇 为溶剂， 反应 7.0h， 以87%的产率得到N-Methyltetrolamid
  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

文献信息

• Rh(III)-Catalyzed (4 + 1) Annulation of Pyrazol-3-ones with Alkynoates via <i>Ortho</i>-Alkenylation/Cyclization Cascade: Synthesis of Indazole-Fused Pyrazoles
  作者：Wei-Jung Chiu、Hong-Ren Chen、Indrajeet J. Barve、Chung-Ming Sun

  DOI：10.1021/acs.joc.2c01208

  日期：2022.9.16

  A facile synthesis of novel indazole-fused pyrazoles from pyrazol-3-ones and alkynoate esters/amides via Rh(III)-catalyzed sequential C–H activation/ortho-alkenylation/intramolecular cyclization cascade is reported. The important characteristic of this method is that the resulting scaffold bearing quaternary carbon has been obtained through unusual [4 + 1] rather than expected [4 + 2] addition where

  报道了通过 Rh(III) 催化的顺序 C-H 活化/邻位-烯基化/分子内环化级联从 pyrazol-3-ones 和炔酸酯/酰胺轻松合成新型吲唑稠合吡唑。该方法的重要特征是所得的带有季碳的支架是通过不寻常的 [4 + 1] 而不是预期的 [4 + 2] 添加获得的，其中炔酸盐充当单碳单元。
• Chemistry and Biology of Deoxynyboquinone, a Potent Inducer of Cancer Cell Death
  作者：Joseph S. Bair、Rahul Palchaudhuri、Paul J. Hergenrother

  DOI：10.1021/ja100610m

  日期：2010.4.21

  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.