(E)-4,5-diphenyl-2-styryl-1H-imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-4,5-diphenyl-2-styryl-1H-imidazole
• 英文别名: 4,5-diphenyl-2-[(E)-2-phenylethenyl]-1H-imidazole
• 化学式: C₂₃H₁₈N₂
• 分子量: 322.409
• InChiKey: IMVYISBBRSGYGM-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  反式肉桂醛 、 联苯甲酰 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以83%的产率得到(E)-4,5-diphenyl-2-styryl-1H-imidazole
  参考文献：
  名称：

  甲酸2-羟乙基铵离子液体接枝的磁性纳米粒子作为新型非均相催化剂，用于合成取代的咪唑

  摘要：

  使用接枝在磁性纳米粒子上的甲酸2-羟乙基铵（HEAF）作为新型多相催化剂，已经成功进行了苯，醛和乙酸铵的催化一锅缩合反应。制备的催化剂通过FT-IR，TEM，FESEM，VSM，TGA和XRD表征。该催化剂显示出显着的优点，例如优异的收率，较短的反应时间，催化剂的可重复使用性和后处理工艺容易。

  DOI：

  10.1002/aoc.4052

文献信息

• Kamlet-Taft and Catalan Studies of Some Novel Y-Shaped Imidazole Derivatives
  作者：J. Jayabharathi、V. Thanikachalam、K. Brindha Devi、M. Venkatesh Perumal

  DOI：10.1007/s10895-011-1009-x

  日期：2012.3

  Some novel Y-shaped imidazole derivatives were developed and characterized by NMR and mass spectral techniques. The photophysical properties of these imidazole derivatives were studied in several solvents. The Kamlet-Taft and Catalan’s solvent scales were found to be the most suitable for describing the solvatochromic shifts of the absorption and fluorescence emission. The adjusted coefficient representing the electron releasing ability or basicity of the solvent, C β or C SB has a negative value, suggesting that the absorption and fluorescence bands shift to lower energies with the increasing electron-donating ability of the solvent. This effect can be interpreted in terms of the stabilization of the resonance structures of the chromophore. The observed lower fluorescence quantum yield may be due to an increase in the non-radiative deactivation rate constant. This is attributed to the loss of planarity in the excited state provided by the non co-planarity of the cinnamaldehyde ring attached to C(2) atom of the imidazole ring. Such a geometrical change in the excited state leads to an important Stokes shift, reducing the reabsorption and reemission effects in the detected emission in highly concentrated solutions.

  开发了一些新颖的Y型咪唑衍生物，并通过NMR和质谱技术对其进行了表征。在多种溶剂中研究了这些咪唑衍生物的光物理性质。研究发现，Kamlet-Taft和Catalan的溶剂标尺最适合描述吸收和荧光发射的溶剂化色移。代表溶剂电子释放能力或碱性的调整系数C β或C SB为负值，表明随着溶剂给电子能力的增强，吸收和荧光谱带向低能方向移动。这一效应可以用发色团共振结构的稳定化来解释。观察到的较低的荧光量子产率可能是由于非辐射失活速率常数的增加。这归因于咪唑环C(2)原子连接的肉桂醛环非共平面性在激发态中导致的平面性损失。这种激发态的几何变化导致重要的斯托克斯位移，减少了在高浓度溶液中的再吸收和再发射效应。
• Nanoparticle-Promoted Synthesis of Trisubstituted Imidazoles in a Green Medium
  作者：Reza Khalifeh、Anahita Niknam

  DOI：10.1080/00304948.2020.1716433

  日期：2020.3.3

  The imidazole ring system is one of the most important heterocyclic substructures and has been found in a large number of pharmacologically active compounds, including the fungicide ketoconazole, the proton pump inhibitor omeprazole, the antiulcerative cimetidine, and the hypnotic agent etomidate. In addition, imidazoles occur in common scaffolds of highly significant biomolecules, including biotin

  咪唑环系是最重要的杂环亚结构之一，已在大量药理活性化合物中发现，包括杀菌剂酮康唑、质子泵抑制剂奥美拉唑、抗溃疡药西咪替丁和催眠药依托咪酯。此外，咪唑存在于非常重要的生物分子的常见支架中，包括生物素、关键氨基酸组氨酸、组胺、毛果芸香碱生物碱以及肌肽和鹅肌肽等二肽。咪唑已被用于聚合物、荧光材料、离子溶剂、N-杂环卡宾化学和摄影中作为光敏化合物。特别是，许多 2,4,5-三取代咪唑被称为杀真菌剂、除草剂、植物生长调节剂、治疗剂、P38MAP 激酶抑制剂、抗菌药和抗惊厥药。2,4,5-三取代咪唑已通过芳基腈与α,α-二硫代芳基硝基甲烷反应或多步合成制备。2,4,5-三取代咪唑通常通过 1,2-二酮、α-羟基酮或α-酮单肟与醛和乙酸铵在催化剂存在下的三组分环缩合反应合成。催化剂包括沸石 HY/硅胶、ZrCl4、20 NiCl2·6H2O、离子液体、碘、亚硫酸氢钠、酸性 Al2O3、25 AcOH、NH4OAc、Yb(OTf)3、27
• Synthesis, Anti-microbial, Antifungal and In Silico Assessment of Some 2,4,5-Trisubstituted Imidazole Analogues
  作者：Elham Zarenezhad、Somayeh Behrouz、Marzieh Behrouz、Mohammad Navid Soltani Rad

  DOI：10.1016/j.molstruc.2023.136839

  日期：2024.1

  In this current research, we have explained design, synthesis and in silico study of some 2,4,5-trisubstituted imidazole derivatives in the presence of [SiO2-CuL] as a heterogeneous catalyst. The chemical structures of title compounds were characterized using different spectroscopic techniques. Then, the in vitro anti-microbial activity of the synthesized compounds 4a-v were investigated against two

  在当前的研究中，我们解释了在[SiO 2 -CuL]作为非均相催化剂存在下一些2,4,5-三取代咪唑衍生物的设计、合成和计算机研究。使用不同的光谱技术表征了标题化合物的化学结构。然后，研究了合成的化合物4a-v针对包括金黄色葡萄球菌（ATCC 6538）和大肠杆菌（ATTC 35218）的两种细菌培养物以及针对一些病原真菌（例如白色念珠菌ATCC 10231）的体外抗微生物活性，光滑念珠菌 (ATCC 2001)、克柔念珠菌 (ATCC 6258)和黑曲霉 (ATCC 16404)。结果表明，与青霉素、四环素和氟康唑对照药相比，这些化合物对上述病原体具有中等到良好的活性。在测试的化合物中，4h对金黄色葡萄球菌和大肠杆菌表现出良好的抗菌活性。此外，4h和4p对光滑念珠菌表现出良好的抗真菌活性（MIC：4 μg/mL），甚至强于标准药物氟康唑（MIC：32 μg/mL）。进行分子对接研究，获得
• PHOTOPROTECTIVE COMPOSITION
  申请人：Apoteknos Para La Piel, S.L.

  公开号：EP2444396A1

  公开（公告）日：2012-04-25

  The present invention relates to a composition comprising (i) a compound A that absorbs in the near visible- ultraviolet A (UVA) region and (ii) a compound B that absorbs in the ultraviolet B (UVB) region, wherein at least one of said compounds A or B is a compound of formula (I) wherein Y represents an optionally substituted aryl or styryl-aryl group, R1, R2, R3 and R4 independently of each other represent H, OH, ORa, NH2, NHRa, NRaRb, NO2 or halogen; wherein Ra and Rb independently of each other represent C1-C10 alkyl; and R5 and R6 independently of each other represent H, or alternatively R5 and R6 together form a C-C bond between the carbon atoms to which they are bound. The invention also relates to the use of said compound of formula (I) in the preparation of a photoprotective composition and to the related cosmetic treatment.

  本发明涉及一种组合物，该组合物包含(i)在近可见光-紫外线A(UVA)区域吸收的化合物A和(ii)在紫外线B(UVB)区域吸收的化合物B，其中所述化合物A或B中至少有一种是式(I)化合物 其中Y代表任选取代的芳基或苯乙烯基芳基，R1、R2、R3和R4彼此独立地代表H、OH、ORa、NH2、NHRa、NRaRb、NO2或卤素；其中 Ra 和 Rb 各自独立地代表 C1-C10 烷基；R5 和 R6 各自独立地代表 H，或者 R5 和 R6 一起在它们所结合的碳原子之间形成 C-C 键。本发明还涉及所述式（I）化合物在制备光保护组合物中的用途以及相关的美容处理。
• Photoinduced electron-transfer from imidazole derivative to nano-semiconductors
  作者：C. Karunakaran、J. Jayabharathi、K. Jayamoorthy、K. Brindha Devi

  DOI：10.1016/j.saa.2011.12.065

  日期：2012.4

  Bioactive imidazole derivative absorbs in the UV region at 305 nm. The interaction of imidazole derivative with nanoparticulate WO3, Fe2O3, Fe3O4, CUO, ZrO2 and Al2O3 has been studied by UV-visible absorption, FT-IR and fluorescence spectroscopies. The imidazole derivative adsorbs strongly on the surfaces of nanosemiconductor, the apparent binding constants for the association between nanomaterials and imidazole derivative have been determined from the fluorescence quenching. In the case of nanocrystalline insulator, fluorescence quenching through electron transfer from the excited state of the imidazole derivative to alumina is not possible. However, a possible mechanism for the quenching of fluorescence by the insulator is energy transfer, that is, energy transferred from the organic molecule to the alumina lattice. Based on Forster's non-radiation energy transfer theory, the distance between the imidazole derivative and nanoparticles (r(0) similar to 2.00 nm) as well as the critical energy transfer distance (R-0 similar to 1.70 nm) has been calculated. The interaction between the imidazole derivative and nanosurfaces occurs through static quenching mechanism. The free energy change (Delta G(et)) for electron transfer process has been calculated by applying Rehm-Weller equation. (C) 2012 Elsevier B.V. All rights reserved.