2-bromo-N-(4-((E)-3-(4-methoxyphenyl)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: 2-bromo-N-(4-((E)-3-(4-methoxyphenyl)acryloyl)phenyl)acetamide
• 英文别名: 2-bromo-N-[4-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]phenyl]acetamide
• 化学式: C₁₈H₁₆BrNO₃
• 分子量: 374.234
• InChiKey: XIJVTXFMNWPNQH-NYYWCZLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  羟甲香豆素 、 2-bromo-N-(4-((E)-3-(4-methoxyphenyl)acryloyl)phenyl)acetamide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以73.77%的产率得到2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-N-(4-((E)-3-(4-methoxyphenyl)acryloyl)phenyl)acetamide
  参考文献：
  名称：

  具有潜在生物活性的新香豆素-查尔酮/ NO杂化物的设计与合成

  摘要：

  摘要这项研究旨在研究一种基于分子杂交策略的合成方法，该方法通过将一氧化氮释放部分肟肟嫁接到香豆素-查耳酮杂种中。某些制备的化合物的体外抗增殖活性显示中等活性（化合物8a对白血病，中枢神经系统和乳腺癌细胞的生长抑制值分别为45.85、40.86、39.25 ）。此外， 化合物8h和8f的IC 50 = 9.62和14.40，分别针对乳腺癌密歇根州癌症基金会7细胞系。抗菌筛查结果表明，一氧化氮可能在增强抗菌活性方面可能发挥作用，其中一氧化氮不是唯一因素，但应研究其他因素（如理化性质）对活性的潜在作用。 图形概要

  DOI：

  10.1007/s00044-017-2004-9
• 作为产物：
  描述：

  4-氨基苯乙酮 在 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 2-bromo-N-(4-((E)-3-(4-methoxyphenyl)acryloyl)phenyl)acetamide
  参考文献：
  名称：

  具有潜在生物活性的新香豆素-查尔酮/ NO杂化物的设计与合成

  摘要：

  摘要这项研究旨在研究一种基于分子杂交策略的合成方法，该方法通过将一氧化氮释放部分肟肟嫁接到香豆素-查耳酮杂种中。某些制备的化合物的体外抗增殖活性显示中等活性（化合物8a对白血病，中枢神经系统和乳腺癌细胞的生长抑制值分别为45.85、40.86、39.25 ）。此外， 化合物8h和8f的IC 50 = 9.62和14.40，分别针对乳腺癌密歇根州癌症基金会7细胞系。抗菌筛查结果表明，一氧化氮可能在增强抗菌活性方面可能发挥作用，其中一氧化氮不是唯一因素，但应研究其他因素（如理化性质）对活性的潜在作用。 图形概要

  DOI：

  10.1007/s00044-017-2004-9

文献信息

• Design and synthesis of novel quinoline/chalcone/1,2,4-triazole hybrids as potent antiproliferative agent targeting EGFR and BRAFV600E kinases
  作者：Aliaa M. Mohassab、Heba A. Hassan、Dalia Abdelhamid、Ahmed M. Gouda、Bahaa G.M. Youssif、Hiroshi Tateishi、Mikako Fujita、Masami Otsuka、Mohamed Abdel-Aziz

  DOI：10.1016/j.bioorg.2020.104510

  日期：2021.1

  New quinoline / chalcone hybrids containing 1,2,4-triazole moiety have been designed, synthesized and their structures elucidated and confirmed by various spectroscopic techniques. The designed compounds showed moderate to good activity on different NCI 60 cell lines in a single-dose assay with a growth inhibition rate ranging from 50% to 94%. Compounds 7b, 7d, 9b, and 9d were the most active compounds

  已经设计、合成了含有 1,2,4-三唑部分的新型喹啉/查耳酮杂化物，并通过各种光谱技术阐明和确认了它们的结构。设计的化合物在单剂量试验中对不同的 NCI 60 细胞系显示出中等至良好的活性，生长抑制率为 50% 至 94%。化合物7b、7d、9b和9d是大多数癌细胞系中活性最强的化合物，其生长抑制百分比在 77% 和 94% 之间。评估了新合成的杂交体对一组四种人类癌细胞系的抗增殖活性。化合物7a、7b、9a、9b和9d显示出有希望的抗增殖活性。以厄洛替尼作为参考药物，进一步测试了这些化合物对 EGFR 和 BRAF V600E激酶的抑制效力。化合物7a、7b、9a、9b和9d的分子对接研究表明，它们非常适合 EGFR 和 BRAF V600E激酶的活性位点。化合物7b、9b和9d显示出最高的结合亲和力和与厄洛替尼相似的结合模式。
• New 1,3,4‐oxadiazole‐chalcone/benzimidazole hybrids as potent antiproliferative agents
  作者：Fatma Fouad Hagar、Samar H. Abbas、Dalia Abdelhamid、Hesham A. M. Gomaa、Bahaa G. M. Youssif、Mohamed Abdel‐Aziz

  DOI：10.1002/ardp.202200357

  日期：2023.2

  (A-549, MCF-7, Panc-1, and HT-29). Compounds 9g–i and their oxygen isosteres, 10f–h, exhibited promising antiproliferative activities with IC50 values ranging from 0.80 to 2.27 µM compared to doxorubicin (IC50 ranging from 0.90 to 1.41 µM). Furthermore, the inhibitory potency of these compounds against the epidermal growth factor receptor (EGFR) and BRAFV600E kinases was evaluated using erlotinib as a

  设计并合成了一系列新的 1,3,4-恶二唑-查耳酮/苯并咪唑杂化物9a-o和10a-k作为潜在的抗增殖剂。杂种9a–o在单剂量测定中对不同的 NCI-60 细胞系表现出显着的抗增殖活性。针对一组四种人类癌细胞系（A-549、MCF-7、Panc-1 和 HT-29）评估了新合成化合物的抗增殖活性。化合物9g–i及其氧等排体10f–h表现出有前途的抗增殖活性，与多柔比星相比， IC 50值范围为 0.80 至 2.27 µM（IC 50范围从 0.90 到 1.41 µM）。此外，使用厄洛替尼作为参考药物评估了这些化合物对表皮生长因子受体 (EGFR) 和 BRAF V600E激酶的抑制效力。进行了分子建模研究以研究 EGFR 的 ATP 结合位点中最活跃的杂合体的结合模式。
• New 1,2,4-triazole-Chalcone hybrids induce Caspase-3 dependent apoptosis in A549 human lung adenocarcinoma cells
  作者：Fatma F. Ahmed、Amer Ali Abd El-Hafeez、Samar H. Abbas、Dalia Abdelhamid、Mohamed Abdel-Aziz

  DOI：10.1016/j.ejmech.2018.03.073

  日期：2018.5

  A series of novel 1, 2, 4-triazole/ichalcone hybrids was prepared and identified with different spectroscopic techniques. The prepared compounds showed remarkable cytotoxic activity against different cancer cell lines. Compounds 24, 25, 27, 41 and 47 had shown the highest cytotoxicity among the tested compounds against human lung adenocarcinoma A549 cells with IC50 ranging from 4.4 to 16.04 mu M compared to cisplatin with IC50 of 153 mu M. Flow cytometric analysis of the tested compounds showed an increase in the number of apoptotic cells in a dose-dependent manner. The further mechanistic study demonstrated that 1, 2, 4-triazole-chalcone hybrids induced apoptosis via increased level of proapoptotic protein Bax, release of cytochrome c from mitochondria and activation of caspase-3/8/9 proteins. However, general caspase inhibition by the pan-caspase inhibitor, z-VAD-fmk, significantly decreased the apoptosis induced by the tested hybrids, suggesting dependency of apoptosis on activation of the caspase-3 pathway. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids: Synthesis, physicochemical properties, anticancer and topoisomerase I and II inhibitory activity
  作者：Mohamed Abdel-Aziz、So-Eun Park、Gamal El-Din A.A. Abuo-Rahma、Mohamed A. Sayed、Youngjoo Kwon

  DOI：10.1016/j.ejmech.2013.08.040

  日期：2013.11

  A group of novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids was prepared. One-dose anticancer test results indicated that compounds 3a and 3g exhibited the highest ability to inhibit the proliferation of different cancer cell lines. Compound 3a exhibited a broad-spectrum of anti-tumor activity without pronounced selectivity while compound 3g revealed high selectivity toward the leukemia subpanel with selectivity ratio of 6.71 at GI(50) level. Moreover, compounds 3e and 3j have shown remarkable topo II inhibitory activity compared to etoposide at 100 gI A and 20 mu M concentrations. Compounds 3e and 3j exhibited comparably potent topo I inhibitory activity at 20 RM concentration compared to camptothecin. Compounds 3e and 3j exhibited strong topo II inhibitory activities compared to topo I at 20 laM concentration. Studying of the solubility and partition coefficient revealed higher lipophilicity of the hybrids 3a j compared to the parent ciprofloxacin. (C) 2013 Elsevier Masson SAS. All rights reserved.
• 1,3,4-oxadiazole/chalcone hybrids: Design, synthesis, and inhibition of leukemia cell growth and EGFR, Src, IL-6 and STAT3 activities
  作者：Marwa Ali A. Fathi、Amer Ali Abd El-Hafeez、Dalia Abdelhamid、Samar H. Abbas、Monica M. Montano、Mohamed Abdel-Aziz

  DOI：10.1016/j.bioorg.2018.11.032

  日期：2019.3

  A new series of 1,3,4-oxadiazole/chalcone hybrids was designed, synthesized, identified with different spectroscopic techniques and biologically evaluated as inhibitors of EGFR, Src, and IL-6. The synthesized compounds showed promising anticancer activity, particularly against leukemia, with 8v being the most potent. The synthesized compounds exhibited strong to moderate cytotoxic activities against K-562, KG-1a, and Jurkat leukemia cell lines in MTT assays. Compound 8v showed the strongest cytotoxic activity with IC50 of 1.95 mu M, 2.36 mu M and 3.45 mu M against K-562, Jurkat and KG-1a leukemia cell lines, respectively. Moreover; the synthesized compounds inhibited EGFR, Src, and IL-6. Compound 8v was most effective at inhibiting EGFR (IC50, = 0.24 mu M), Src (IC50 = 0.96 mu M), and IL-6 (% of control = 20%). Additionally, most of the compounds decreased STAT3 activation.