(E)-N-(3,5-dimethoxyphenyl)-3-(4-hydroxyphenyl)acrylamide | 1227263-02-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-N-(3,5-dimethoxyphenyl)-3-(4-hydroxyphenyl)acrylamide
• 英文别名: (E)-N-(3,5-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-enamide
• CAS: 1227263-02-6
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: AEXRTSWATLNLML-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-香豆酸 、 3,5-二甲氧基苯胺 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以17%的产率得到(E)-N-(3,5-dimethoxyphenyl)-3-(4-hydroxyphenyl)acrylamide
  参考文献：
  名称：

  Phenylcinnamides as Novel Antimitotic Agents

  摘要：

  Compound 8H is a phenylcinnamide that induces G2/M-phase cell cycle arrest and cell death in cancer cell lines. Here we show that 811 exerts its cytotoxic activity through disruption of microtubule dynamics in vitro and in cell culture. A series of cinnamide derivatives were synthesized and evaluated, and several new compounds were identified that improve on the activity of the parent compound, with IC(50) values for induction of cell death ranging from 1 to 10 mu M. Notably, these compounds retain potency in the HL-60/VCR leukemia cell line, which is resistant to antimitotic cancer drugs vincrisitine and paclitaxel through up-regulation of P-glycoprotein drug efflux pumps. As P-glycoprotein expression is often responsible for drug resistance in cancer and the exclusion of compounds from the central nervous system, 8H and its derivatives merit further examination as potential antimitotic therapeutics, specifically for brain cancers and cancers that are resistant to standard antimitotic agents.

  DOI：

  10.1021/jm901805m

文献信息

• Phenylcinnamides as Novel Antimitotic Agents
  作者：Benjamin J. Leslie、Clinton R. Holaday、Tran Nguyen、Paul J. Hergenrother

  DOI：10.1021/jm901805m

  日期：2010.5.27

  Compound 8H is a phenylcinnamide that induces G2/M-phase cell cycle arrest and cell death in cancer cell lines. Here we show that 811 exerts its cytotoxic activity through disruption of microtubule dynamics in vitro and in cell culture. A series of cinnamide derivatives were synthesized and evaluated, and several new compounds were identified that improve on the activity of the parent compound, with IC(50) values for induction of cell death ranging from 1 to 10 mu M. Notably, these compounds retain potency in the HL-60/VCR leukemia cell line, which is resistant to antimitotic cancer drugs vincrisitine and paclitaxel through up-regulation of P-glycoprotein drug efflux pumps. As P-glycoprotein expression is often responsible for drug resistance in cancer and the exclusion of compounds from the central nervous system, 8H and its derivatives merit further examination as potential antimitotic therapeutics, specifically for brain cancers and cancers that are resistant to standard antimitotic agents.