(E)-2-chloro-N-(4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)acetamide

• 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: (E)-2-chloro-N-(4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)acetamide
• 英文别名: 2-chloro-N-[4-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]phenyl]acetamide
• 化学式: C₂₀H₂₀ClNO₅
• 分子量: 389.835
• InChiKey: XMTAIORDSGMRNM-RUDMXATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-2-chloro-N-(4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)acetamide 、 对羟基苯甲醛 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 以72 %的产率得到2-(4-formylphenoxy)-N-(4-((E)-3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)acetamide
  参考文献：
  名称：

  新型查尔酮衍生物的合成、计算机抗病毒筛选和体外抗菌筛选

  摘要：

  DOI：

  10.1016/j.jics.2023.101038
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (E)-2-chloro-N-(4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)acetamide
  参考文献：
  名称：

  作为抗增殖剂的氨基查耳酮衍生物的合成和生物学评价

  摘要：

  查耳酮是在许多生物活性化合物中发现的常见支架。查耳酮支架也经常用于设计具有强大生物功效的新型抗癌剂。为了继续研究有效的查尔酮衍生物来治疗癌症，具有强大的抗癌活性，设计并合成了十四种氨基查尔酮衍生物。体外研究氨基查尔酮衍生物的抗增殖活性，5-Fu 作为对照组。一些化合物对三种人类癌细胞（MGC-803、HCT-116 和 MCF-7 细胞）显示出中等至良好的活性，化合物 13e 对 MGC-803 细胞、HCT-116 细胞和 MCF-7 显示出最好的抗增殖活性IC50 值为 1.52 μM (MGC-803)、1.83 μM (HCT-116) 和 2.54 μM (MCF-7) 的细胞，分别比阳性对照（5-Fu）更有效。进一步的机制研究进行了探索。细胞集落形成试验的结果表明化合物10e抑制MGC-803细胞的集落形成。DAPI 荧光染色和流式细胞术检测显示化合物 13e 诱导 MGC-803

  DOI：

  10.3390/molecules25235530

文献信息

• Synthesis and Biological Evaluation of Amino Chalcone Derivatives as Antiproliferative Agents
  作者：Chao-Fan Lu、Sheng-Hui Wang、Xiao-Jing Pang、Ting Zhu、Hong-Li Li、Qing-Rong Li、Qian-Yu Li、Yu-Fan Gu、Zhao-Yang Mu、Min-Jie Jin、Yin-Ru Li、Yang-Yang Hu、Yan-Bing Zhang、Jian Song、Sai-Yang Zhang

  DOI：10.3390/molecules25235530

  日期：——

  Chalcone is a common scaffold found in many biologically active compounds. The chalcone scaffold was also frequently utilized to design novel anticancer agents with potent biological efficacy. Aiming to continue the research of effective chalcone derivatives to treat cancers with potent anticancer activity, fourteen amino chalcone derivatives were designed and synthesized. The antiproliferative activity

  查耳酮是在许多生物活性化合物中发现的常见支架。查耳酮支架也经常用于设计具有强大生物功效的新型抗癌剂。为了继续研究有效的查尔酮衍生物来治疗癌症，具有强大的抗癌活性，设计并合成了十四种氨基查尔酮衍生物。体外研究氨基查尔酮衍生物的抗增殖活性，5-Fu 作为对照组。一些化合物对三种人类癌细胞（MGC-803、HCT-116 和 MCF-7 细胞）显示出中等至良好的活性，化合物 13e 对 MGC-803 细胞、HCT-116 细胞和 MCF-7 显示出最好的抗增殖活性IC50 值为 1.52 μM (MGC-803)、1.83 μM (HCT-116) 和 2.54 μM (MCF-7) 的细胞，分别比阳性对照（5-Fu）更有效。进一步的机制研究进行了探索。细胞集落形成试验的结果表明化合物10e抑制MGC-803细胞的集落形成。DAPI 荧光染色和流式细胞术检测显示化合物 13e 诱导 MGC-803
• Synthesis, antimicrobial, anti-biofilm evaluation, and molecular modelling study of new chalcone linked amines derivatives
  作者：Shahenda M. El-Messery、El-Sayed E. Habib、Sarah T. A. Al-Rashood、Ghada S. Hassan

  DOI：10.1080/14756366.2018.1461855

  日期：2018.1.1

  strain Staphylococcus aureus. The products were screened for anti-biofilm activity. Compounds 36, 37, and 38 exhibited promising anti-biofilm activity with IC50 value ranges from 2.4 to 8.6 µg. Molecular modelling was performed suggesting parameters of signalling anti-biofilm mechanism. AspB327 HisB340 (arene-arene interaction) and IleB328 amino acid residues seemed of higher importance to inhibit c-di-GMP

  合成了一系列与不同仲胺结合的酰胺查耳酮，并通过不同的光谱技术对其进行了表征：1 H NMR，13 C NMR和ESI-MS。筛选它们的体外抗菌活性。在合成系列中，化合物36、37、38、42和44活性最高，对不同细菌菌株的MIC值为2.0-10.0 µg / ml。化合物36与标准药物氨苄西林等价，对细菌菌株金黄色葡萄球菌的MBC值为2.0 µg / ml。筛选产品的抗生物膜活性。化合物36、37和38表现出令人鼓舞的抗生物膜活性，IC50值为2.4至8.6 µg。进行分子建模，提示信号抗生物膜机制的参数。AspB327 HisB340（芳烃-芳烃相互作用）和IleB328氨基酸残基似乎对抑制c-di-GMP具有更高的重要性。疏水性可能对活动至关重要。ADME计算表明，化合物36、37和38可用作良​​好的口服吸收抗生物膜剂。
• Design, synthesis, and anti-hepatocellular carcinoma of thiopyrimidine/chalcone hybrids as dual STAT3/STAT5 inhibitors
  作者：Najla Altwaijry、Rehab Sabour、Mona H. Ibrahim、Omkulthom Al kamaly、Omeima Abdullah、Marwa F. Harras

  DOI：10.1039/d3md00300k

  日期：——

  therapeutic targets for treating cancer are the continuously active STAT proteins, which are important in the progression of many malignancies. Here, we detail the STAT3/5 inhibitory action and thiopyrimidine/chalcone hybrid design, production, and anti-hepatocellular carcinoma activity. The prepared hybrids were assessed for their cytotoxic effect on HepG2 and Huh7 liver cancer cells. The most active

  持续活跃的 STAT 蛋白是治疗癌症的有希望的治疗靶标之一，它在许多恶性肿瘤的进展中发挥着重要作用。在这里，我们详细介绍了 STAT3/5 的抑制作用以及硫代嘧啶/查尔酮杂化物的设计、生产和抗肝细胞癌活性。评估制备的杂交体对 HepG2 和 Huh7 肝癌细胞的细胞毒性作用。最活跃的化合物5e和5h （IC 50范围为 0.55 至 2.58 μM）针对正常 THLE 细胞进行了进一步评估，以检查其安全性。另外还测试了杂交体5e和5h抑制 STAT3 和 STAT5a 的潜力。它们表现出双重抑制作用，与​​对照相比，STAT3 水平分别降低了 65 倍和 87 倍，STAT5 水平分别降低了 60 倍和 79.5 倍。此外，化合物5h的蛋白质印迹分析显示，STAT3 和 STAT5 在 Tyr705 和 Tyr694 处的磷酸化分别受到抑制，STAT3 和 STAT5 蛋白的总表达仅略有下降。最后，分子对接研究为
• Discovery of novel AHLs as potent antiproliferative agents
  作者：Jing-Li Ren、Xu-Yao Zhang、Bin Yu、Xi-Xin Wang、Kun-Peng Shao、Xiao-Ge Zhu、Hong-Min Liu

  DOI：10.1016/j.ejmech.2015.02.026

  日期：2015.3

  Three series of novel AHL analogs were synthesized and evaluated for their in vitro cytotoxic activity against four human cancer cell lines. The SARs investigation indicated that AHLs with a terminal phenyl group, especially those with the chalcone scaffold had remarkably enhanced cytotoxicity than those with the hydrophobic side chains. Besides, some of these compounds were much more potent than 5-Fu and natural OdDHL. Through the detailed SARs discussions, we found that compounds 10a-k and 14 with the 4-amino chalcone scaffold showed excellent inhibition against all the tested cancer cell lines and were much more potent than 5-Fu and AHLs. Such scaffold may act as a template for further lead optimization. Compound 10i with a 3, 4, 5-trimethoxy group was the most potent one against all the tested cancer cell lines. Flow cytometry analysis indicated that analog lie induced the cellular apoptosis and cell cycle arrest of MCF-7 cells at G2/M phase in a concentration-and time-dependent manner. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Discovery of novel chalcone-dithiocarbamates as ROS-mediated apoptosis inducers by inhibiting catalase
  作者：Dong-Jun Fu、Jia-Huan Li、Jia-Jia Yang、Ping Li、Yan-Bing Zhang、Simeng Liu、Zhong-Rui Li、Sai-Yang Zhang

  DOI：10.1016/j.bioorg.2019.01.023

  日期：2019.5

  Novel chalcone-dithiocarbamate hybrids were designed, synthesized and evaluated for antiproliferative activity against selected cancer cell lines (MGC803, MCF7, and PC3). Among these analogues, (E)-2-oxo-2-((4-(3-(3,4,5-trimethoxyphenyl) acryloyl) phenyl) amino) ethyl-4-(2-hydroxyethyl) piperazine-1-carbodithioate (12d) showed the best inhibitory activity against PC3 cells (IC50 = 1.05 mu M). Cellular mechanism studies elucidated 12d could inhibit colony formation, arrest cell cycle at G2/M phase and induce DNA damage against PC3 cells. Compound 12d also induced mitochondrial apoptosis by caspase activation, MMP decrease, ROS production and catalase (CAT) inhibition. Importantly, 12d inhibited epithelial-mesenchymal transition (EMT) process by regulating EMT-related proteins (E-cadherin, N-cadherin, Vimentin, MMP2, MMP9). These results indicated that 12d is a promising lead compound and deserves further investigation for prevention and treatment of human prostate cancer.