3-(4-bromophenyl)-1-(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: 3-(4-bromophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one
• 英文别名: 1-(3,4-Dimethoxyphenyl)-3-(4-bromophenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₅BrO₃
• 分子量: 347.208
• InChiKey: AQCGUPISNITRRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-bromophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 5-(4-bromophenyl)-3-(3,4-dimethoxyphenyl)-1-(4-sulfamoylphenyl)-1H-pyrazole
  参考文献：
  名称：

  Synthesis of novel halogenated triarylpyrazoles as selective COX-2 inhibitors: Anti-inflammatory activity, histopatholgical profile and in-silico studies

  摘要：

  A novel series of halogenated triarylpyrazoles 12a-l was designed and synthesized. All target compounds showed good in vitro COX-2 inhibitory activity (IC₅₀ = 0.043-0.17 µM) over COX-1 (IC₅₀ = 7.8 - 15.4 µM) relative to celecoxib (COX-1/IC₅₀ = 9.87, COX-2/IC₅₀ = 0.055), with acceptable selectivity index values (SI = 50.6-253.1). Also, they displayed moderate to potent in vivo anti-inflammatory activity (% edema inhibition = 16.9-87.9) comparable to celecoxib (% edema inhibition = 46.6-72.1) as standard drug. Three fluorinated pyrazoles 12a, 12g and 12j, exhibited superior anti-inflammatory activity at all time intervals (% edema inhibition = 42.1-87.9) with better gastric profile (UI = 1.25-2.5) than the traditional NSAID; indomethacin (UI = 14) and were close to the selective COX-2 inhibitor; celecoxib (UI = 1.75). In-silico docking and ADME studies of 12a, 12g and 12j supported the obtained biological data and pointed out their potential use for the development of bio-available, safe and potent anti-inflammatory drugs.

  DOI：

  10.1016/j.bioorg.2020.104418
• 作为产物：
  描述：

  对溴苯甲醛 、 3,4-二甲氧基苯乙酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 20.0h， 生成 3-(4-bromophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  设计，合成和4,6-二苯基嘧啶-2-胺衍生物用于抑制Aurora激酶A的多酚的生物学评估。

  摘要：

  背景技术几种4，6-二芳基嘧啶-2-胺衍生物显示出抗癌特性。但是，它们的作用方式尚未完全表征。为了开发有效的抗癌化学治疗剂，我们设计并合成了25个含有胍基部分的4,6-二苯基嘧啶-2-胺衍生物。方法进行了长期克隆存活试验以筛选抗癌化合物。为了得出对癌细胞具有良好细胞毒性的结构条件，计算了定量构效关系（QSAR）。通过流式细胞术测定生物活性以进行细胞周期分析，并通过免疫印迹分析测定Aurora激酶A（AURKA）活性。由于2-（2-氨基-6-（2,4-二甲氧基苯基）嘧啶-4-基）苯酚（衍生物12）通过kinome分析选择性抑制AURKA活性，在计算机对接实验中进行了阐明衍生物12和AURKA之间的分子结合模式。结果药效基团是基于QSAR计算得出的。衍生物12抑制了HCT116人结肠癌细胞在Thr283处的AURKA活性并降低了AURKA的磷酸化。衍生物12引起细胞周期G2 / M期的积累，并

  DOI：

  10.1007/s40199-019-00272-5

文献信息

• Design, synthesis, and biological evaluation of polyphenols with 4,6-diphenylpyrimidin-2-amine derivatives for inhibition of Aurora kinase A
  作者：Young Han Lee、Jihyun Park、Seunghyun Ahn、Youngshim Lee、Junho Lee、Soon Young Shin、Dongsoo Koh、Yoongho Lim

  DOI：10.1007/s40199-019-00272-5

  日期：2019.6

  cytotoxicities against cancer cells, quantitative structure-activity relationships (QSAR) were calculated. Biological activities were determined by flow cytometry for cell cycle analysis and by immunoblot analysis for the detection of Aurora kinase A (AURKA) activity. Because 2-(2-Amino-6-(2,4-dimethoxyphenyl)pyrimidin-4-yl) phenol (derivative 12) selectively inhibited AURKA activity from the kinome assay

  背景技术几种4，6-二芳基嘧啶-2-胺衍生物显示出抗癌特性。但是，它们的作用方式尚未完全表征。为了开发有效的抗癌化学治疗剂，我们设计并合成了25个含有胍基部分的4,6-二苯基嘧啶-2-胺衍生物。方法进行了长期克隆存活试验以筛选抗癌化合物。为了得出对癌细胞具有良好细胞毒性的结构条件，计算了定量构效关系（QSAR）。通过流式细胞术测定生物活性以进行细胞周期分析，并通过免疫印迹分析测定Aurora激酶A（AURKA）活性。由于2-（2-氨基-6-（2,4-二甲氧基苯基）嘧啶-4-基）苯酚（衍生物12）通过kinome分析选择性抑制AURKA活性，在计算机对接实验中进行了阐明衍生物12和AURKA之间的分子结合模式。结果药效基团是基于QSAR计算得出的。衍生物12抑制了HCT116人结肠癌细胞在Thr283处的AURKA活性并降低了AURKA的磷酸化。衍生物12引起细胞周期G2 / M期的积累，并
• Design, Synthesis, and Structural Elucidation of New Pyridine and Thienopyridine Derivatives
  作者：Mohamed A. Elsayed、Naglaa A. Abdel Hafez、Manal M. Elshahawi、Korany A. Ali

  DOI：10.1002/jhet.3392

  日期：2019.1

  New series of 3‐cyanopyridine scaffolds were prepared from the reaction of 3‐(4‐bromophenyl)‐1‐(3,4‐dimethoxyphenyl)prop‐2‐en‐1‐one with active nitriles, including malononitrile and 2‐cyanothioacetamide. The newly prepared 6‐(4‐bromophenyl)‐4‐(3,4‐dimethoxyphenyl)‐2‐thioxo‐1,2‐dihydropyridine‐3‐carbonitrile was used as a scaffold for the preparation of new series of condensed thienopyridines by its

  通过3-（4-溴苯基）-1-（3,4-二甲氧基苯基）丙-2-烯-1-酮与活性腈（包括丙二腈和2-氰基硫代乙酰胺）的反应制备了一系列新的3-氰基吡啶骨架。新制备的6-（4-溴苯基）-4-（3,4-二甲氧基苯基）-2-硫代-1,2-二氢吡啶-3-3-腈被用作制备新系列缩合噻吩并吡啶的骨架与活性卤素化合物的反应，即氯乙酸乙酯，氯乙腈，苯甲酰溴，氯丙酮和2-氯-N-芳基乙酰胺。通过元素分析，光谱数据和通过其他途径制备的化学方法阐明了合成化合物的结构。
• Synthesis of novel halogenated triarylpyrazoles as selective COX-2 inhibitors: Anti-inflammatory activity, histopatholgical profile and in-silico studies
  作者：Khaled R.A. Abdellatif、Eman K.A. Abdelall、Madlen B. Labib、Wael A.A. Fadaly、Taha H. Zidan

  DOI：10.1016/j.bioorg.2020.104418

  日期：2020.12

  A novel series of halogenated triarylpyrazoles 12a-l was designed and synthesized. All target compounds showed good in vitro COX-2 inhibitory activity (IC₅₀ = 0.043-0.17 µM) over COX-1 (IC₅₀ = 7.8 - 15.4 µM) relative to celecoxib (COX-1/IC₅₀ = 9.87, COX-2/IC₅₀ = 0.055), with acceptable selectivity index values (SI = 50.6-253.1). Also, they displayed moderate to potent in vivo anti-inflammatory activity (% edema inhibition = 16.9-87.9) comparable to celecoxib (% edema inhibition = 46.6-72.1) as standard drug. Three fluorinated pyrazoles 12a, 12g and 12j, exhibited superior anti-inflammatory activity at all time intervals (% edema inhibition = 42.1-87.9) with better gastric profile (UI = 1.25-2.5) than the traditional NSAID; indomethacin (UI = 14) and were close to the selective COX-2 inhibitor; celecoxib (UI = 1.75). In-silico docking and ADME studies of 12a, 12g and 12j supported the obtained biological data and pointed out their potential use for the development of bio-available, safe and potent anti-inflammatory drugs.