(1E,3E,5E)-1,6-bis(3,4-dimethoxyphenyl)hexa-1,3,5-triene | 70022-70-7

• 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: (1E,3E,5E)-1,6-bis(3,4-dimethoxyphenyl)hexa-1,3,5-triene
• 英文别名: 1,6-Bis (3,4-dimethoxyphenyl)-1,3,5-hexatrien；4-[(1E,3E,5E)-6-(3,4-dimethoxyphenyl)hexa-1,3,5-trienyl]-1,2-dimethoxybenzene
• CAS: 70022-70-7
• 化学式: C₂₂H₂₄O₄
• 分子量: 352.43
• InChiKey: UWVAAULFCPNVCZ-NRIIQWGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-dimethoxycinnamaldehyde 在 beryllium,ethanone,bromide 作用下， 生成 (1E,3E,5E)-1,6-bis(3,4-dimethoxyphenyl)hexa-1,3,5-triene
  参考文献：
  名称：

  Lapkin,I.I. et al., Journal of general chemistry of the USSR, 1979, vol. 49, p. 146 - 148

  摘要：

  DOI：

文献信息

• Molecular Docking Studies of (1<i>E</i>,3<i>E</i>,5<i>E</i>)-1,6-Bis(substituted phenyl)hexa-1,3,5-triene and 1,4-Bis(substituted <i>trans</i>-styryl)benzene Analogs as Novel Tyrosinase Inhibitors
  作者：Young Mi Ha、Hye Jin Lee、Daeui Park、Hyoung Oh Jeong、Ji Young Park、Yun Jung Park、Kyung Jin Lee、Ji Yeon Lee、Hyung Ryong Moon、Hae Young Chung

  DOI：10.1248/bpb.b12-00605

  日期：——

  We simulated the docking of the tertiary structure of mushroom tyrosinase with our compounds. From the structure-tyrosinase inhibitory activity relationship, it is notable that compounds 4, 8 and 11 showed similar or better activity rates than kojic acid which was used as a positive control. Compounds 17, 21, and 23 among benzene analogs that possess the same substituent showed significantly lower tyrosinase inhibitory effects. Therefore, we have confirmed that among the compounds showing better tyrosinase inhibitory effects than kojic acid, the compounds with triene analogs have better tyrosinase inhibitory effect than the compounds with benzene analogs. Docking simulation suggested the mechanism of compounds by several key residues which had possible hydrogen bonding interactions. The pharmacophore model underlined the features of active compounds, 4,4′-((1E,3E,5E)-hexa-1,3,5-triene-1,6-diyl)diphenol, 5,5′-((1E,3E,5E)-hexa-1,3,5-triene-1,6-diyl)bis(2-methoxy-phenol), and 5,5′-((1E,3E,5E)-hexa-1,3,5-triene-1,6-diyl)dibenzene-1,3-diol among triene derivatives which had several hydrogen bond groups on both terminal rings. The soundness of the docking results and the agreement with the pharmacophores suggest that it can be conveniently exploited to design inhibitors with an improved affinity for tyrosinase.

  我们模拟了蘑菇酪氨酸酶三维结构与我们的化合物的对接。从结构-酪氨酸酶抑制活性关系来看，化合物4、8和11显示出的活性与作为阳性对照的曲酸相似或更好。在具有相同取代基的苯类类似物中，化合物17、21和23的酪氨酸酶抑制效果显著较低。因此，我们确认在显示出比曲酸更好的酪氨酸酶抑制效果的化合物中，含有三烯类似物的化合物的酪氨酸酶抑制效果优于含有苯类类似物的化合物。对接模拟通过几个可能形成氢键相互作用的关键残基提出了化合物的作用机制。药效团模型强调了活性化合物的特征，包括4,4′-((1E,3E,5E)-己-1,3,5-三烯-1,6-二醇)二苯酚、5,5′-((1E,3E,5E)-己-1,3,5-三烯-1,6-二醇)双(2-甲氧基苯酚)和5,5′-((1E,3E,5E)-己-1,3,5-三烯-1,6-二醇)二苯-1,3-二醇，这些三烯衍生物在两个末端环上具有多个氢键基团。对接结果的合理性以及与药效团的吻合表明，可以方便地利用这些信息设计具有更强酪氨酸酶亲和力的抑制剂。
• Lapkin,I.I. et al., Journal of general chemistry of the USSR, 1979, vol. 49, p. 146 - 148
  作者：Lapkin,I.I. et al.

  DOI：——

  日期：——