(2E,2'E)-3,3'-(1,4-phenylene)bis(1-(4-methoxyphenyl)prop-2-en-1-one) | 143517-15-1

• 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-(4-methoxyphenyl)prop-2-en-1-one)
• 英文别名: (2E,2'E)-3,3'-(1,4-Phenylene)bis[1-(4-methoxyphenyl)prop-2-en-1-one]；(E)-1-(4-methoxyphenyl)-3-[4-[(E)-3-(4-methoxyphenyl)-3-oxoprop-1-enyl]phenyl]prop-2-en-1-one
• CAS: 143517-15-1
• 化学式: C₂₆H₂₂O₄
• 分子量: 398.458
• InChiKey: IFZFXZVMGMTYEE-ZEELXFFVSA-N

物化性质

• 沸点：
  614.2±55.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E,2'E)-3,3'-(1,4-phenylene)bis(1-(4-methoxyphenyl)prop-2-en-1-one) 在 sodium hydroxide 、 苄基三乙基氯化铵 、 双氧水 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  Reddy, D. Bhaskar; Seenaiah, B.; Padmavathi, V., Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 69, # 1-2, p. 31 - 42

  摘要：

  DOI：
• 作为产物：
  描述：

  对苯二甲醛 、 对甲氧基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以51%的产率得到(2E,2'E)-3,3'-(1,4-phenylene)bis(1-(4-methoxyphenyl)prop-2-en-1-one)
  参考文献：
  名称：

  荧光双(苯基呋喃基)苯的快速合成

  摘要：

  通过双 Mn(OAc) 3催化氧化脱羰和β-酮酯，由乙酰乙酸乙酯与对-和间-双（查耳酮）的共轭加成制备。对于具有邻-甲氧基取代的间-双(苯基呋喃基)苯观察到较强的荧光强度，而对于具有对-甲氧基取代的对-双(苯基呋喃基)苯观察到较长的荧光波长。

  DOI：

  10.1055/a-1941-1535

文献信息

• Synthesis and evaluation of the anticancer activity of bischalcone analogs in human lung carcinoma (A549) cell line
  作者：Jie Yang、Wen-Wen Mu、Guo-Yun Liu

  DOI：10.1016/j.ejphar.2020.173396

  日期：2020.12

  because of its wide range of application in pharmaceutical chemistry. This work aims to evaluate the antiproliferation effects and explore the anticancer mechanism of bischalcone analogs on human lung cancer A549 cells. In this study, we synthesized a series of bischalcone analogs via Aldol condensation reaction; MTT method was used to evaluate the antiproliferation effects; the 2′,7′-dichlorofluorescein

  Bischalcone由于在药物化学中的广泛应用而备受关注。这项工作旨在评估抗扩散作用，并探索比沙可康类似物对人肺癌A549细胞的抗癌机制。在这项研究中，我们通过Aldol缩合反应合成了一系列比沙可康类似物。采用MTT法评价其抗增殖作用。用2'，7'-二氯荧光素荧光法测定细胞内活性氧的含量。谷胱甘肽还原酶-DTNB回收法检测氧化还原失衡。硫代巴比妥酸反应性物质的测定用于评估脂质过氧化作用；若丹明123用于测试线粒体膜电位（MMP）；FITC / PI试剂盒用于检测细胞凋亡。1d和1g化合物比姜黄素稳定性更高，在A549细胞中的效能比姜黄素和其他比沙可康类似物高得多。进一步的作用机理研究表明1d和1g具有比姜黄素更高的活性氧生成能力，并伴有氧化还原失衡，脂质过氧化，MMP丢失，Bax和Caspase 3活化，最终导致A549凋亡细胞。这些数据表明，增强比沙可康类似物的活性氧物种生成能力可能是治疗人类肺癌的有前途的策略。
• Ultrasound-assisted synthesis of novel chalcone, heterochalcone and bis-chalcone derivatives and the evaluation of their antioxidant properties and as acetylcholinesterase inhibitors
  作者：Efraín Polo、Nicol Ibarra-Arellano、Luis Prent-Peñaloza、Alejandro Morales-Bayuelo、José Henao、Antonio Galdámez、Margarita Gutiérrez

  DOI：10.1016/j.bioorg.2019.103034

  日期：2019.9

  The chalcone and bis-chalcone derivatives have been synthesized under sonication conditions via Claisen-Schmidt condensation with KOH in ethanol at room temperature (20-89%). The structures were established on the basis of NMR, IR, Single-crystal XRD, and MS. The best compound 3u had inhibitory activity (IC50 = 7.50 µM). The synthesis, the antioxidative properties, chemical reactivity descriptors supported

  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。
• 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。
• 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.
• Symmetric Bis-chalcones as a New Type of Breast Cancer Resistance Protein Inhibitors with a Mechanism Different from That of Chromones
  作者：Evelyn Winter、Patrícia Devantier Neuenfeldt、Louise Domeneghini Chiaradia-Delatorre、Charlotte Gauthier、Rosendo Augusto Yunes、Ricardo José Nunes、Tânia Beatriz Creczynski-Pasa、Attilio Di Pietro

  DOI：10.1021/jm401879z

  日期：2014.4.10

  Potent ABCG2 inhibitors were recently identified as asymmetric chromones with different types of substituents. We here synthesized symmetric bis-chalcones that were differently substituted and screened for their ability to inhibit mitoxantrone efflux from ABCG2-transfected HEK293 cells. Potent bis-chalcone inhibitors were identified, the efficiency depending on both position of the central ketone groups and the number and positions of lateral methoxy substituents. The best derivative, namely, 1p, was selective for ABCG2 over P-glycoprotein and MRP1, appeared not to be transported by ABCG2, and was at least as active on various drug-selected cancer cells overexpressing ABCG2. Compound 1p stimulated the ABCG2 basal ATPase activity by contrast to a chromone lead that inhibited it, suggesting different mechanisms of interaction. Combination of both types of inhibitors produced synergistic effects, leading to complete inhibition at very low