(E)-4-(4-羟基苯乙烯)吡啶 | 67882-97-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (E)-4-(4-羟基苯乙烯)吡啶
• 英文名称: 4-[(E)-2-(4-pyridinyl)ethenyl]phenol
• 英文别名: 4-[(E)-2-(pyridin-4-yl)ethenyl]phenol；trans-4-hydroxy-4'-stilbazole；(E)-γ-azastilbenol-4'；(E)-4-(4-Hydroxystyryl)pyridine；4-[(E)-2-pyridin-4-ylethenyl]phenol
• CAS: 67882-97-7
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: NZSWYXAQUBELKN-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-(4-羟基苯乙烯)吡啶 在 甲醇 、 镍 作用下， 80.0~90.0 ℃ 、9.81 MPa 条件下， 生成 1-(4-hydroxyphenyl)-2-(4-pyridyl)ethane
  参考文献：
  名称：

  X-Ray Diagnostics. VI. Diiodohydroxydihydrostilbazoles and Related Compounds

  摘要：

  DOI：

  10.1021/ja01145a085
• 作为产物：
  描述：

  4-((E)-4-(2,4-dinitrophenoxy)styryl)pyridine 在 sodium sulfide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 (E)-4-(4-羟基苯乙烯)吡啶
  参考文献：
  名称：

  2,4-dinitrophenyl ether-containing chemodosimeters for the selective and sensitive ‘in vitro’ and ‘in vivo’ detection of hydrogen sulfide

  摘要：

  Four probes (i.e. D1-D4) for the selective and sensitive fluorogenic detection of HS- have been prepared and characterised. HEPES (10mM, pH 7.4)-DMSO 99:1 v/v solutions of D1-D4 are essentially non-fluorescent. Changes in the emission using D1-D4 in the presence of anions (F-, Cl-, Br-, I-,[GRAPHICS], CN-, SCN-, AcO-,[GRAPHICS],[GRAPHICS],[GRAPHICS], HS- and OH-), biothiols (GSH, Cys, Hcy, Me-Cys and lipoic acid), reducing agents ([GRAPHICS]and[GRAPHICS]) and oxidants (H2O2) demonstrated that only HS- is able to induce the appearance of intense emission bands in the 400-520nm range in the four probes. The selectivity observed was ascribed to a unique hydrogen sulfide-induced hydrolysis of the 2,4-dinitrophenyl ether moiety that yielded the corresponding free highly fluorescent alcohols. The potential detection of intracellular HS- was also studied.

  DOI：

  10.1080/10610278.2014.977286

文献信息

• Synthesis and Anti-inflammatory Activity of Resveratrol Analogs
  作者：Guoliang Chen、Wei Shan、Yingliang Wu、Lixiang Ren、Jinhua Dong、Zhizhong Ji

  DOI：10.1248/cpb.53.1587

  日期：——

  Seventeen novel resveratrol derivatives were synthesized. Their anti-inflammatory activities were tested on xylene-induced mouse ear edema. The pharmacological results showed that some compounds have potent anti-inflammatory activities.

  合成了17种新型的白藜芦醇衍生物。在二甲苯诱导的小鼠耳肿胀模型上测试了它们的抗炎活性。药理学结果显示，其中一些化合物具有强大的抗炎活性。
• Synthesis and cytotoxic effects on pancreatic cancer cells of resveratrol analogs
  作者：Barbara De Filippis、Laura De Lellis、Rosalba Florio、Alessandra Ammazzalorso、Pasquale Amoia、Marialuigia Fantacuzzi、Letizia Giampietro、Cristina Maccallini、Rosa Amoroso、Serena Veschi、Alessandro Cama

  DOI：10.1007/s00044-019-02351-3

  日期：2019.7

  pancreatic cancer cell lines were evaluated. The new molecules were designed by removing the 3- and 5-OH groups of resveratrol, and by incorporating other substituents in 4-position, or by replacing the dihydroxybenzene with other aromatic systems. In all compounds the 4′-OH was kept unalterated. The effects of the compounds on cell viability were analyzed in three pancreatic cancer cell lines with

  在这项研究中，合成了一系列白藜芦醇类似物，并评估了其对胰腺癌细胞系活力的影响。通过除去白藜芦醇的3-和5-OH基团，并通过在4-位引入其他取代基，或通过用其他芳族体系取代二羟基苯来设计新分子。在所有化合物中，4'-OH均保持不变。在三种具有不同遗传特征的胰腺癌细胞系中分析了这些化合物对细胞活力的影响。几种化合物（例如，5，9，和12相比于参比化合物）显示出改善的细胞毒活性，使得它们是进一步评估作为抗癌药物的潜在候选。
• Tuning the photonic properties of chiral nematic mesoporous organosilica with hydrogen-bonded liquid-crystalline assemblies
  作者：Michael Giese、Tim Krappitz、Ronald Y. Dong、Carl A. Michal、Wadood Y. Hamad、Brian O. Patrick、Mark J. MacLachlan

  DOI：10.1039/c4tc02602k

  日期：——

  The thermochromic behaviour of chiral nematic mesoporous organosilica hybrids infiltrated with hydrogen-bonded liquid crystals was investigated by polarized optical microscopy, UV-vis and CD-spectroscopy.

  手性向列介孔有机硅杂化材料与氢键液晶的热致变色行为通过偏振光学显微镜、紫外可见光谱和圆二色光谱进行了研究。
• Hydrogen bonding and the design of twist-bend nematogens
  作者：Rebecca Walker、Damian Pociecha、Catriona A. Crawford、John M.D. Storey、Ewa Gorecka、Corrie T. Imrie

  DOI：10.1016/j.molliq.2020.112630

  日期：2020.4

  Neither hydrogen bond acceptor exhibits liquid crystal behaviour whereas the nOBA compounds show smectic and/or nematic behaviour depending on the length of the alkyloxy chain. For the complexes of an nOBA with n = 1–5, both conventional nematic and twist-bend nematic phases were observed, while for n ≥ 6 smectic phases emerged and the twist-bend nematic phase was extinguished. The CB6OS-nOBA mixtures may

  由氢键供体，4-烷氧基苯甲酸（n OBA）和两种不同的基于stilbazole的氢键受体之一（4-[（E）-2-（4-[ 6-（4'-甲氧基[1,1'-联苯] -4-基）己基]氧基}苯基）-乙烯基]-吡啶（1OB6OS）或4-[（E）-4'-（6- 4报道了-[[（E）-2-（吡啶-4-基）乙烯基]苯氧基}己基）-[1,1'-联苯] -4-腈（CB6OS）。氢键受体均不表现出液晶行为，而n OBA化合物根据烷氧基链的长度不表现出近晶和/或向列行为。对于n  = 1–5的n OBA的络合物，可以观察到常规的向列相和扭曲弯曲向列相，而对于n 出现≥6个近晶相，并消除了扭曲-弯曲向列相。CB6OS- n OBA混合物可能呈现螺旋近晶C TB相。两组混合物中的局部分子排列相似，并且随着n的增加而变化，但这未反映在向列各向同性转变温度中。报道了混合物的双折射研究。通常，氢键合混合物的行为类似于其共价键合对应物的行为。
• PPARα agonists based on stilbene and its bioisosteres: biological evaluation and docking studies
  作者：Barbara De Filippis、Mariangela Agamennone、Alessandra Ammazzalorso、Isabella Bruno、Alessandra D'Angelo、Mauro Di Matteo、Marialuigia Fantacuzzi、Letizia Giampietro、Antonella Giancristofaro、Cristina Maccallini、Rosa Amoroso

  DOI：10.1039/c5md00151j

  日期：——

  A new series of gemfibrozil analogues conjugated with trans-stilbene were synthesized and evaluated with the aim of developing new PPARα agonists. The phenyls of stilbene were modified by introducing substituents in the ortho or para position and only the distal ring was substituted with naphthyl or heteroaromatic moieties, keeping the dimethylpentanoic skeleton of gemfibrozil unaltered. Two compounds

  为了开发新的PPARα激动剂，合成并评估了一系列新的与反式-二苯乙烯缀合的吉非贝齐类似物。通过在邻位或对位引入取代基来修饰二苯乙烯的苯基，并且仅远端环被萘基或杂芳族部分取代，从而保持了吉非贝齐的二甲基戊酸骨架不变。两种化合物5a和5d表现出良好的PPARα活化作用，还筛选了它们对PPARα调控的基因CPT1A的活性。对活性配体进行的基于结构的研究突出了配体溶剂化能和疏水效应在确定PPARα活化中的主导作用。

表征谱图