(2E,2'E)-1,1'-(1,3-phenylene)bis(3-(3,4-dimethoxyphenyl)prop-2-en-1-one)

• 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)-1,1'-(1,3-phenylene)bis(3-(3,4-dimethoxyphenyl)prop-2-en-1-one)
• 英文别名: 1′,3′-bis-(E/E)-[3-(3′′,4′′-dimethoxyphenyl)-1-oxo-2-enyl]-benzene；(E)-3-(3,4-dimethoxyphenyl)-1-[3-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]phenyl]prop-2-en-1-one
• 化学式: C₂₈H₂₆O₆
• 分子量: 458.511
• InChiKey: DBECJLKRPJOGNU-QHKWOANTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E,2'E)-1,1'-(1,3-phenylene)bis(3-(3,4-dimethoxyphenyl)prop-2-en-1-one) 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以61%的产率得到(2E,2'E)-1,1'-(1,3-phenylene)bis(3-(3,4-dihydroxyphenyl)prop-2-en-1-one)
  参考文献：
  名称：

  Analogues of xanthones——Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates

  摘要：

  Two series of compounds (chalcones and bis-chalcones) were designed, synthesized, and evaluated as aglucosidase inhibitors (AGIs) with 1-deoxynojirimycin as positive control in vitro. Most of the compounds with two or four hydroxyl groups showed better inhibitory activities than 1-deoxynojirimycin towards aglucosidase with noncompetitive mechanism. Moreover, most of the hydroxy bis-chalcones exhibit good a-glucosidase inhibitory activities in enzyme test. Inspiringly, bis-chalcones 2g (at 1 mu M concentration) has stronger effect than 1-deoxynojirimycin on reducing the glucose level in HepG-2 cells (human liver cancer cell line). (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.007
• 作为产物：
  描述：

  1,3-二乙酰基苯 、 3,4-二甲氧基苯甲醛 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以33%的产率得到(2E,2'E)-1,1'-(1,3-phenylene)bis(3-(3,4-dimethoxyphenyl)prop-2-en-1-one)
  参考文献：
  名称：

  Analogues of xanthones——Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates

  摘要：

  Two series of compounds (chalcones and bis-chalcones) were designed, synthesized, and evaluated as aglucosidase inhibitors (AGIs) with 1-deoxynojirimycin as positive control in vitro. Most of the compounds with two or four hydroxyl groups showed better inhibitory activities than 1-deoxynojirimycin towards aglucosidase with noncompetitive mechanism. Moreover, most of the hydroxy bis-chalcones exhibit good a-glucosidase inhibitory activities in enzyme test. Inspiringly, bis-chalcones 2g (at 1 mu M concentration) has stronger effect than 1-deoxynojirimycin on reducing the glucose level in HepG-2 cells (human liver cancer cell line). (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.007

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。
• 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.