1,6-bis(p-methoxyphenyl)hexa-1,3,5-triene | 36288-04-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,6-bis(p-methoxyphenyl)hexa-1,3,5-triene
• 英文别名: (1E,3E,5E)-1,6-bis(4-methoxyhenyl)hexa-1,3,5-triene；(1E,3E,5E)-1,6-bis(4-methoxyphenyl)hexa-1,3,5-triene；1,6-bis(4-methoxyphenyl)hexa-1,3,5-triene；1,6-Bis (p-methoxyphenyl)-1,3,5-hexatrien；MeO-DPH；1,6-Bis(4''-methoxyphenyl)-hexa-1,3,5-triene；1-methoxy-4-[(1E,3E,5E)-6-(4-methoxyphenyl)hexa-1,3,5-trienyl]benzene
• CAS: 36288-04-7
• 化学式: C₂₀H₂₀O₂
• 分子量: 292.378
• InChiKey: ZZEXRQNWFCTKHJ-OKWWDJPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,6-bis(p-methoxyphenyl)hexa-1,3,5-triene 在 碘 作用下， 以 苯 为溶剂， 生成 3,9-dimethoxy-chrysene
  参考文献：
  名称：

  Photocyclization Reactions of Aryl Polyenes. V. Photochemical Synthesis of Substituted Chrysenes

  摘要：

  1,6-二对位取代苯基-1,3,5-己三烯的光环化-氧化反应产生了3,9-二取代蒽。类似地，对1-对位取代苯基-6-苯基-1,3,5-己三烯的辐射处理产生了3-取代蒽。通过1-α-萘基-2-对位取代苯乙烯的光环化-氧化，高产率地独立制备了3-取代蒽。

  DOI：

  10.1139/v72-081
• 作为产物：
  描述：

  4-甲氧基肉桂醛 在 beryllium,ethanone,bromide 作用下， 生成 1,6-bis(p-methoxyphenyl)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。
• 1,6-Dibromohexa-1,3,5-triene − Stereocontrolled Synthesis of Monosubstituted and Disubstituted Hexatrienes by Palladium-Catalysed Cross-Coupling Reactions
  作者：Pierre Villiers、Nicolas Vicart、Yvan Ramondenc、Gérard Plé

  DOI：10.1002/1099-0690(200102)2001:3<561::aid-ejoc561>3.0.co;2-r

  日期：2001.2

  a versatile precursor for the synthesis of conjugated 1,3,5-trienic derivatives of controlled configuration. In this paper, we describe the stereocontrolled synthesis of E,E,Z, E,E,E and Z,E,Z isomers of α-bromo-ω-substituted-1,3,5-hexatrienes and 1,6-disubstituted-1,3,5-hexatrienes. The synthesis is based on palladium-catalysed single or double cross-coupling reactions between the three isomers − 1E

  1，6-二溴己六，1，3，5-三烯是我们先前所描述的，可通过与溴亚甲基三苯基磷烷缩合而从5-溴戊二-2，4-二烯容易地获得，是合成共轭1,3受控构型的5-三烯衍生物。在本文中，我们描述了α-溴-ω-取代-1,3,5-己三烯和1,6-二取代的E，E，Z，E，E，E和Z，E，Z异构体的立体控制合成-1,3,5-己三烯。合成基于钯催化的三种异构体-1 E， 3 E， 5 Z，1 E， 3 E， 5 E和1 Z之间的单或双交叉偶联反应，中间体1,6-二溴己-1,3,5-三烯和各种有机锌试剂的3 E， 5 Z-。
• Stilbene derivatives and their use for binding and imaging amyloid plaques
  申请人：Kung F. Hank

  公开号：US20060269474A1

  公开（公告）日：2006-11-30

  This invention relates to a method of imaging amyloid deposits and to labeled compounds, and methods of making labeled compounds useful in imaging amyloid deposits. This invention also relates to compounds, and methods of making compounds for inhibiting the aggregation of amyloid proteins to form amyloid deposits, and a method of delivering a therapeutic agent to amyloid deposits.

  本发明涉及一种成像淀粉样沉积物的方法，以及标记化合物和制备标记化合物的方法，以用于成像淀粉样沉积物。此外，本发明还涉及化合物和制备化合物的方法，以抑制淀粉样蛋白聚集形成淀粉样沉积物，并将治疗剂递送到淀粉样沉积物的方法。
• Practical and Convenient Synthesis of 1,6-Di- or 1,2,5,6-Tetra-arylhexa-1,3,5-trienes by the Dimerization of Pd(0)-Complexed Alkenylcarbenes Generated from π-Allylpalladium Intermediates
  作者：Yoshikazu Horino、Yu Takahashi、Kaori Koketsu、Hitoshi Abe、Kiyoshi Tsuge

  DOI：10.1021/ol501643x

  日期：2014.6.20

  Pd(0)-complexed 3-aryl or 2,3-diaryl propenylcarbenes generated from alpha-silyl-, alpha-germyl-, or alpha-boryl-alpha-allylpalladium intermediates undergo self-dimerization to provide 1,6-di or 1,2,5,6-tetraarylhexa-1,3,5-trienes in good to high yields. This method allows the use of a pi-allylpalladium intermediate for a carbenoid precursor. Furthermore, the obtained 1,2,5,6-tetraarylhexa-1,3,5-trienes exhibit aggregation-induced emission enhancement property.
• Synthesis of Biphenyltrienes as Probes for β-Amyloid Plaques
  作者：Zhi-Ping Zhuang、Mei-Ping Kung、Hank F. Kung

  DOI：10.1021/jm051020k

  日期：2006.5.1

  We report a series of p-hydroxy-, p-amino-, p-monomethylamino-, and p-monofluoroethylamino-substituted biphenyltrienes that displayed high binding affinities to beta-amyloid plaques. In an in vitro binding assay using postmortem brain homogenates of Alzheimer's patients and [I-125] 9, the triene compounds showed excellent binding affinities. When labeled with suitable radionuclides, they are useful as in vivo imaging agents for detecting A beta plaques in the brains of Alzheimer's patients.