(E)-5–(4-(octyloxy)styryl)benzene-1,3-diol | 190371-61-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-5–(4-(octyloxy)styryl)benzene-1,3-diol
• 英文别名: 5-[(E)-2-(4-octoxyphenyl)ethenyl]benzene-1,3-diol
• CAS: 190371-61-0
• 化学式: C₂₂H₂₈O₃
• 分子量: 340.463
• InChiKey: XXMXETVSVUAMAT-CMDGGOBGSA-N

物化性质

• 沸点：
  515.8±19.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5–(4-(octyloxy)styryl)benzene-1,3-diol 在 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (E)-3,3’-((5–(4-(octyloxy)styryl)-1,3-phenylene)bis(oxy))bis(propan-1-amine)
  参考文献：
  名称：

  受阳离子肽启发的氨基烷基白藜芦醇衍生物的合成及抗菌活性

  摘要：

  摘要 抗菌素耐药性是一个全球性问题，远未得到解决。针对新靶标的新药的需求迫在眉睫。在这项工作中，我们展示了一系列具有抗菌活性的氨基烷基白藜芦醇衍生物，其灵感来自阳离子两亲性抗菌肽的特性。令人惊讶的是，新设计的分子对需氧生长的细菌表现出适度的活性，但对厌氧菌（革兰氏阴性和革兰氏阳性）表现出令人惊讶的良好抗菌活性，表明对该细菌群具有特异性。对作用机制的初步研究表明，活性发生在膜水平，而没有观察到与传统抗生素的交叉耐药性。实际上，在对抗革兰氏阴性病原体方面发现了与现有抗生素的一些良好协同关系。然而，尽管它们的溶血活性低，但仍观察到一些细胞毒性。我们的结果表明带正电荷的部分和疏水性之间的平衡对于提高抗菌活性的重要性，为基于这些分子的新药设计奠定了基础。

  DOI：

  10.1080/14756366.2022.2146685
• 作为产物：
  描述：

  3,5-二甲氧基苄醇 在 sodium methylate 、 三溴化磷 、 二苯基膦酸锂 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-5–(4-(octyloxy)styryl)benzene-1,3-diol
  参考文献：
  名称：

  双（二苯乙烯基）方晶—具有扩展共轭作用的新型颜料

  摘要：

  我们报告了一种新型的方晶（11a-f，17c）的合成，其中发色团的共轭由二苯乙烯单元扩展。这些颜料表现出吸收带，该吸收带的最大值在Vis区域的末端，并部分到达NIR。

  DOI：

  10.1016/0040-4039(95)02414-x

文献信息

• Chemical modifications of resveratrol for improved protein kinase C alpha activity
  作者：Joydip Das、Satyabrata Pany、Anjoy Majhi

  DOI：10.1016/j.bmc.2011.08.008

  日期：2011.9

  Resveratrol (1) is a naturally occurring phytoalexin that affects a variety of human disease models, including cardio-and neuroprotection, immune regulation, and cancer chemoprevention. One of the possible mechanisms by which resveratrol affects these disease states is by affecting the cellular signaling network involving protein kinase C alpha (PKC alpha). PKC alpha is a member of the family of serine/threonine kinases, whose activity is inhibited by resveratrol. To study the structure-activity relationship, several monoalkoxy, dialkoxy and hydroxy analogs of resveratrol have been synthesized, tested for their cytotoxic effects on HEK293 cells, measured their effects on the membrane translocation properties of PKC alpha in the presence and absence of the PKC activator TPA, and studied their binding with the activator binding domain of PKC alpha. The analogs showed less cytotoxic effects on HEK293 cells and caused higher membrane translocation (activation) than that of resveratrol. Among all the analogs, 3, 16 and 25 showed significantly higher activation than resveratrol. Resveratrol analogs, however, inhibited phorbol ester-induced membrane translocation, and the inhibition was less than that of resveratrol. Binding studies using steady state fluorescence spectroscopy indicated that resveratrol and the analogs bind to the second cysteine-rich domain of PKC alpha. The molecular docking studies indicated that resveratrol and the analogs interact with the protein by forming hydrogen bonds through its hydroxyl groups. These results signify that molecules developed on a resveratrol scaffold can attenuate PKC alpha activity and this strategy can be used to regulate various disease states involving PKC alpha. (C) 2011 Elsevier Ltd. All rights reserved.
• Extension of the Squaraine Chromophore in Symmetrical Bis(stilbenyl)squaraines
  作者：Herbert Meier、Uta Dullweber

  DOI：10.1021/jo970284e

  日期：1997.7.1

  The bis(stilbenyl)squaraines 6d-j,d',j' represent a novel class of NIR pigments. Their synthesis was performed by the regioselective 2-fold condensation of highly nucleophilic 3,5-dihydroxystilbenes 4d-j,d'j' with squaric acid (5). Depending on the substitution with alkoxy groups, the absorption maxima range in solution from 680 to 735 nm. Reflexion measurements in the solid state reveal an exciton splitting with maxima at about 670 and 1000 nm.
• Bis(stilbenyl)squaraines — Novel pigments with extended conjugation
  作者：Herbert Meier、Uta Dullweber

  DOI：10.1016/0040-4039(95)02414-x

  日期：1996.2

  We report on the synthesis of a novel type of squaraines (11a-f, 17c) in which the conjugation of the chromophore is extended by stilbene units. These pigments exhibit absorption bands which have their maxima at the end on the Vis region and reach partly into the NIR.

  我们报告了一种新型的方晶（11a-f，17c）的合成，其中发色团的共轭由二苯乙烯单元扩展。这些颜料表现出吸收带，该吸收带的最大值在Vis区域的末端，并部分到达NIR。
• Synthesis and antimicrobial activity of aminoalkyl resveratrol derivatives inspired by cationic peptides
  作者：Rubén Cebrián、Ricardo Lucas、María Victoria Fernández-Cantos、Koen Slot、Pablo Peñalver、Marta Martínez-García、Antonio Párraga-Leo、María Violante de Paz、Federico García、Oscar P. Kuipers、Juan Carlos Morales

  DOI：10.1080/14756366.2022.2146685

  日期：2023.12.31

  concern, far from being resolved. The need of new drugs against new targets is imminent. In this work, we present a family of aminoalkyl resveratrol derivatives with antibacterial activity inspired by the properties of cationic amphipathic antimicrobial peptides. Surprisingly, the newly designed molecules display modest activity against aerobically growing bacteria but show surprisingly good antimicrobial

  摘要 抗菌素耐药性是一个全球性问题，远未得到解决。针对新靶标的新药的需求迫在眉睫。在这项工作中，我们展示了一系列具有抗菌活性的氨基烷基白藜芦醇衍生物，其灵感来自阳离子两亲性抗菌肽的特性。令人惊讶的是，新设计的分子对需氧生长的细菌表现出适度的活性，但对厌氧菌（革兰氏阴性和革兰氏阳性）表现出令人惊讶的良好抗菌活性，表明对该细菌群具有特异性。对作用机制的初步研究表明，活性发生在膜水平，而没有观察到与传统抗生素的交叉耐药性。实际上，在对抗革兰氏阴性病原体方面发现了与现有抗生素的一些良好协同关系。然而，尽管它们的溶血活性低，但仍观察到一些细胞毒性。我们的结果表明带正电荷的部分和疏水性之间的平衡对于提高抗菌活性的重要性，为基于这些分子的新药设计奠定了基础。