(2E,2′E)-3,3′-(1,4-phenylene)bis(1-(p-tolyl)prop-2-en-1-one) | 146492-34-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2E,2′E)-3,3′-(1,4-phenylene)bis(1-(p-tolyl)prop-2-en-1-one)
• 英文别名: 1′,4′-bis-(E/E)-[1-(4′′-methylphenyl)-prop-1-oxo-2-enyl]benzene；(2E,2'E)-3,3'-(1,4-phenylene)bis(1-p-tolylprop-2-en-1-one)；(2E)-1-(4-Methylphenyl)-3-{4-[(1E)-3-(4-methylphenyl)-3-oxoprop-1-en-1-yl]phenyl}prop-2-en-1-one；(E)-1-(4-methylphenyl)-3-[4-[(E)-3-(4-methylphenyl)-3-oxoprop-1-enyl]phenyl]prop-2-en-1-one
• CAS: 146492-34-4
• 化学式: C₂₆H₂₂O₂
• 分子量: 366.459
• InChiKey: RQGINYHSPFFVKT-JYFOCSDGSA-N

物化性质

• 沸点：
  577.6±50.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,2′E)-3,3′-(1,4-phenylene)bis(1-(p-tolyl)prop-2-en-1-one) 、 (benzoylmethylene)dimethylsulfurane 以 苯 为溶剂， 反应 40.0h， 以68%的产率得到
  参考文献：
  名称：

  Reddy, D Bhaskar; Seenaiah, B; Padmavathi, V, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 8, p. 503 - 506

  摘要：

  DOI：
• 作为产物：
  描述：

  对苯二甲醛 、 对甲基苯乙酮 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以82%的产率得到(2E,2′E)-3,3′-(1,4-phenylene)bis(1-(p-tolyl)prop-2-en-1-one)
  参考文献：
  名称：

  超声辅助合成新型查尔酮，杂查尔酮和双查尔酮衍生物，并评估其抗氧化性能和作为乙酰胆碱酯酶抑制剂。

  摘要：

  查尔酮和双查尔酮衍生物是在超声条件下，通过Claisen-Schmidt与KOH在乙醇中于室温下缩合（20-89％）合成的。基于NMR，IR，单晶XRD和MS建立结构。最好的化合物3u具有抑制活性（IC50 = 7.50 µM）。通过分子对接吗啉-查耳酮和喹啉-查耳酮预测了合成，抗氧化性能，密度泛函理论（DFT）支持的化学反应性描述子，乙酰胆碱酯酶（AChE）抑制及其潜在的结合模式和亲和力。还报道了一系列的双查耳酮。化合物3u的分子对接和酶动力学研究表明，它同时与AChE的催化活性位点（CAS）和外围阴离子位点（PAS）结合。

  DOI：

  10.1016/j.bioorg.2019.103034

文献信息

• Design, synthesis and drug resistance reversal potential of novel curcumin mimics Van D
  作者：Gaurav Raj Dwivedi、Sadiya Khwaja、Arvind Singh Negi、Swati S. Panda、A. Swaroop Sanket、Sanghamitra Pati、Amit Chand Gupta、Dnyaneshwar Umrao Bawankule、Debabrata Chanda、Rajni Kant、Mahendra P. Darokar

  DOI：10.1016/j.bioorg.2020.104454

  日期：2021.1

  crucial part of plant-based novel discovery of drug from natural resources, a study was done to explore the antibacterial potential of curcumin mimics in combination with antibiotics against multidrug resistant isolates of Pseudomonas aeruginosa. The best candidate Van D, a curcumin mimics reduced the MIC of tetracycline (TET) up to 16 folds against multidrug resistant clinical isolates. VanD further inhibited

  作为以植物为基础的自然资源新药物发现的关键部分，一项研究旨在探索姜黄素模拟物与抗生素联合对抗铜绿假单胞菌多药耐药菌株的抗菌潜力。最好的候选药物Van D，姜黄素模拟物将四环素 (TET) 对多药耐药临床分离株的 MIC 降低了 16 倍。VanD 进一步抑制了外排泵，如溴化乙锭外排和计算机对接研究所证明的那样。在另一项实验中，还发现Van D抑制生物膜合成。这种衍生物可杀死 KG-P2，一种铜绿假单胞菌的分离物以时间依赖性方式，四环素的抗生素后效应（PAE）延长，TET的突变预防浓度（MPC）也降低。在瑞士白化小鼠中，Van D降低了促炎细胞因子的浓度。在急性口服毒性研究中，该衍生物具有良好的耐受性，并发现高达 1000 mg/kg 的剂量是安全的。据我们所知，这是关于姜黄素模拟物通过抑制外排泵作为增效剂的第一份报告。
• Synthesis and properties of n-type triphenylpyridine derivatives and applications in deep-blue organic light-emitting devices as electron-transporting layer
  作者：Na Li、Shiu-Lun Lai、Weimin Liu、Pengfei Wang、Juanjuan You、Chun-Sing Lee、Zengtao Liu

  DOI：10.1039/c1jm11898f

  日期：——

  Two series of n-type triphenylpyridine derivatives with good thermal properties and efficient deep-blue emissions were designed, synthesized and systematically characterized. Most of them show high glass transition temperatures (Tg > 100 °C), relatively high electron mobilities, large ionization potentials (IP > 6.31 eV) and suitable electron affinities (EA > 2.93 eV) for facilitating efficient electron-injection. These attributes of the n-type triphenylpyridine derivatives favours their applications in organic light-emitting devices (OLEDs) as electron-transporting and hole-blocking materials (ETMs and HBMs). With these new materials, deep-blue OLEDs with a configuration of indium-tin oxide (ITO)/α-napthylphenylbiphenyl diamine (NPB)/9,10-di(2-naphthyl)anthracene (ADN)/triphenylpyridine derivative/LiF/MgAg were fabricated to investigate the properties of these triphenylpyridine derivatives as ETMs and HBMs. The devices show higher efficiency (2.54 cd A−1), and better color purity (0.15, 0.10) compared to those of similarly-structured blue OLEDs using state-of-the-art ETMs. The large IP and deep-blue emission of the triphenylpyridine derivatives are considered to be key factors for the higher efficiencies and better color purity. Optical and other properties of the compounds are discussed in terms of their molecular structures.

  我们设计、合成并系统表征了两个系列的 n 型三苯基吡啶衍生物，它们具有良好的热性能和高效的深蓝色发射。它们大多具有较高的玻璃化转变温度（Tg > 100 °C）、相对较高的电子迁移率、较大的电离电位（IP > 6.31 eV）和合适的电子亲和力（EA > 2.93 eV），有利于高效电子注入。n 型三苯基吡啶衍生物的这些特性有利于它们作为电子传输和空穴阻断材料（ETM 和 HBM）应用于有机发光器件（OLED）。利用这些新材料，制备了铟锡氧化物（ITO）/α-萘基联苯二胺（NPB）/9,10-二（2-萘基）蒽（ADN）/三苯基吡啶衍生物/LiF/MgAg 构型的深蓝色 OLED，以研究这些三苯基吡啶衍生物作为 ETM 和 HBM 的特性。与使用最先进 ETM 的类似结构蓝色 OLED 相比，这些器件显示出更高的效率（2.54 cd A-1）和更好的色纯度（0.15、0.10）。三苯基吡啶衍生物的大 IP 值和深蓝色发射被认为是效率更高、色纯度更好的关键因素。本文从分子结构的角度讨论了这些化合物的光学特性和其他特性。
• Antiproliferative efficacy of curcumin mimics through microtubule destabilization
  作者：Sadiya Khwaja、Kaneez Fatima、Mohammad Hasanain、Chittaranjan Behera、Avneet Kour、Arjun Singh、Suaib Luqman、Jayanta Sarkar、Debabrata Chanda、Karuna Shanker、A.K. Gupta、D.M. Mondhe、Arvind S. Negi

  DOI：10.1016/j.ejmech.2018.03.063

  日期：2018.5

  Curcumin possesses an attractive chemical structure with highly conjugated diferuloylmethane core. Curcumin mimics have been designed and prepared with an additional bridged phenyl ring in conjugation. Fourteen diverse analogues were evaluated against a panel of human cancer cell lines. The best analogue of the series i.e. compound 6a exhibited potent cytotoxicity against A431, epidermoid carcinoma cell line (IC50 = 1.5 mu M) and DLDI, colorectal adenocarcinoma cell line (IC50 = 6.9 mu M). In tubulin kinetics experiment, compound 6a destabilized polymerisation process (IC50 = 4.68 mu M). In cell cycle analysis, compound 6a exerted G2/M phase arrest in A431 cells and induced apoptosis. In Ehrlich Ascites Carcinoma in Swiss-albino mice, compound 6a showed 78.6% tumour reduction at 80 mg/kg dose and 57% solid tumour reduction at 150 mg/kg dose. Further, in acute-oral toxicity experiment in rodent model, compound 6a was given in three different oral doses to Swiss albino mice. There were nonsignificant changes in various biochemical parameters and major body organs studied, including their absolute and relative weights. It was tolerable up to 300 mg/kg dose in Swiss -albino mice. The present study shows that the novel curcumin mimic 6a is a safe and efficacious anticancer compound. However, it needs to be optimized for better efficacy. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Bhaskar Reddy; Seenaiah; Muralidhar Reddy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 10, p. 1012 - 1016
  作者：Bhaskar Reddy、Seenaiah、Muralidhar Reddy

  DOI：——

  日期：——
• Bhaskar Reddy; Seshamma; Reddy, Journal of the Indian Chemical Society, 1991, vol. 68, # 5, p. 281 - 284
  作者：Bhaskar Reddy、Seshamma、Reddy、Ramana Reddy

  DOI：——

  日期：——