(E)-1-(4-fluorophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one | 1002175-72-5

• 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)-1-(4-fluorophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one
• 英文别名: (E)-1-(4-fluorophenyl)-3-naphthalen-2-ylprop-2-en-1-one
• CAS: 1002175-72-5
• 化学式: C₁₉H₁₃FO
• 分子量: 276.31
• InChiKey: KXEDVEHGTNJKHC-WUXMJOGZSA-N

物化性质

• 沸点：
  451.2±45.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-fluorophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成 22-((E)-4-(4-(3-(naphthalen-2-yl)acryloyl)phenyl)piperazin-1-yl)-22-deoxypleuromutilin
  参考文献：
  名称：

  新型查尔酮-胸膜泌尿素衍生物的合成，生物活性和对接研究。

  摘要：

  这些天，抗生素抗性问题变得越来越严重，解决该问题的可行解决方案是开发和发现新型抗生素。二萜天然截短侧耳素因其通过抑制蛋白质合成的特殊作用方式而成为重要候选者。在这项研究中，设计和合成了一系列具有查耳酮部分的截短侧耳素新衍生物，并在体外评估了它们的抗菌活性。结果表明，大多数化合物对两种耐甲氧西林的金黄色葡萄球菌均具有有效的活性。（MRSA）ATCC 33591和43300。随后对查尔酮结构，氮杂环衍生物进行了进一步修饰，然后进行了评估，并报道了其对测试菌株的有效活性。进行了初步的对接研究，以探索目标分子与结合位点之间的相互作用。

  DOI：

  10.1111/cbdd.13692
• 作为产物：
  描述：

  4-氟苯乙酮 、 2-萘甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (E)-1-(4-fluorophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one
  参考文献：
  名称：

  新型查尔酮-胸膜泌尿素衍生物的合成，生物活性和对接研究。

  摘要：

  这些天，抗生素抗性问题变得越来越严重，解决该问题的可行解决方案是开发和发现新型抗生素。二萜天然截短侧耳素因其通过抑制蛋白质合成的特殊作用方式而成为重要候选者。在这项研究中，设计和合成了一系列具有查耳酮部分的截短侧耳素新衍生物，并在体外评估了它们的抗菌活性。结果表明，大多数化合物对两种耐甲氧西林的金黄色葡萄球菌均具有有效的活性。（MRSA）ATCC 33591和43300。随后对查尔酮结构，氮杂环衍生物进行了进一步修饰，然后进行了评估，并报道了其对测试菌株的有效活性。进行了初步的对接研究，以探索目标分子与结合位点之间的相互作用。

  DOI：

  10.1111/cbdd.13692

文献信息

• Design, modification and 3D QSAR studies of novel naphthalin-containing pyrazoline derivatives with/without thiourea skeleton as anticancer agents
  作者：Wen Yang、Yang Hu、Yu-Shun Yang、Fei Zhang、Yan-Bin Zhang、Xiao-Liang Wang、Jian-Feng Tang、Wei-Qing Zhong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2013.01.013

  日期：2013.3

  Two series of novel naphthalin-containing pyrazoline derivatives C1-C14 and D1-D14 have been synthesized and evaluated for their EGFR/HER-2 inhibitory and anti-proliferation activities. Compound D14 displayed the most potent activity against EGFR and A549 cell line (IC50 = 0.05 mu M and GI(50) = 0.11 mu M), being comparable with the positive control Erlotinib (IC50 = 0.03 mu M and GI(50) = 0.03 mu M) and more potent than our previous compounds C0-A (IC50 = 5.31 mu M and GI(50) = 33.47 mu M) and C0-B (IC50 = 0.09 mu M and GI(50) = 0.34 mu M). Meanwhile, compound C14 displayed the most potent activity against HER-2 and MCF-7 cell line (IC50 = 0.88 mu M and GI(50) = 0.35 mu M), being a little less potent than Erlotinib (IC50 = 0.16 mu M and GI(50) = 0.08 mu M) but far more potent than C0-A (IC50 = 6.58 mu M and GI(50) = 27.62 mu M) and C0-B (IC50 = 2.77 mu M and GI(50) = 3.79 mu M). The docking simulation was performed to analyze the probable binding models and the QSAR models were built for reasonable design of EGFR/HER-2 inhibitors at present and in future. The structural modification of introducing naphthalin moiety reinforced the combination of our compounds and the receptor, resulting in progress of bioactivity. Moreover, the replacement of thiourea skeleton by using benzene ring resulted in the slight diversity of the two series towards specific targets. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of Renoprotective Chalcone Analogues That Protect Against Cisplatin-induced Cytotoxicity in LLC-PK1 Cells
  作者：Noriko Yamabe、Dahae Lee、Heesu Lee、Myung Sook Shin、Gwi Seo Hwang、Ki Sung Kang、Jae Wook Lee

  DOI：10.1002/bkcs.10984

  日期：2016.11
• Synthesis of (αR,βS)-epoxyketones by asymmetric epoxidation of chalcones with cinchona phase-transfer catalysts
  作者：Mi-Sook Yoo、Dong-Guk Kim、Min Woo Ha、Sang-sup Jew、Hyeung-geun Park、Byeong-Seon Jeong

  DOI：10.1016/j.tetlet.2010.08.056

  日期：2010.10

  An efficient method to synthetically produce optically enriched (alpha R,beta S)-epoxyketones was developed using a quaternary ammonium salt derived from cinchona alkaloid as the chiral phase-transfer catalyst. (alpha R,beta S)-Epoxyketones were prepared in high optical purities (91-99% ee) by the asymmetric epoxidation of 1,3-diarylenones with aqueous sodium hypochlorite in the presence of a hydrocinchonine-derived chiral phase-transfer catalyst bearing a 2,3,4-trifluorobenzyl group. (C) 2010 Elsevier Ltd. All rights reserved.
• Regioselective [3+2] cycloaddition of chalcones with a sugar azide: easy access to 1-(5-deoxy-d-xylofuranos-5-yl)-4,5-disubstituted-1H-1,2,3-triazoles
  作者：Nimisha Singh、S.K. Pandey、Rama P. Tripathi

  DOI：10.1016/j.carres.2010.04.019

  日期：2010.8

  [3+2] Cycloaddition of 5-azido-5-deoxy-1,2-O-isopropylidene-alpha-D-xylofuranose with 1,3-diphenylprop-3-enones, followed by oxidation of the intermediate triazolines in a tandem manner, led to the regioselective formation of 4-benzoyl-1-(5-deoxy-1,2-O-isopropylidene-alpha-D-xylofuranos-5-yl)-5-phenyl-1H-1,2,3-triazoles in moderate to good yields. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis, biological activities, and docking study of novel chalcone‐pleuromutilin derivatives
  作者：Chuan Xie、Siyu Zhang、Wei Zhang、Chunxia Wu、Can Yong、Yuhao Sun、Zhengxing Zeng、Qian Zhang、Zixin Huang、Tian Chen、Yuanyuan Zhang

  DOI：10.1111/cbdd.13692

  日期：2020.8

  discover novel antibiotics. The diterpene natural pleuromutilin is a prominent candidate for its special mode of action by inhibiting protein synthesis. In this study, a series of novel pleuromutilin derivatives with chalcone moiety was designed and synthesized, and their antibacterial activities were assessed in vitro. As suggested from the results, most of compounds exhibited potent activities against

  这些天，抗生素抗性问题变得越来越严重，解决该问题的可行解决方案是开发和发现新型抗生素。二萜天然截短侧耳素因其通过抑制蛋白质合成的特殊作用方式而成为重要候选者。在这项研究中，设计和合成了一系列具有查耳酮部分的截短侧耳素新衍生物，并在体外评估了它们的抗菌活性。结果表明，大多数化合物对两种耐甲氧西林的金黄色葡萄球菌均具有有效的活性。（MRSA）ATCC 33591和43300。随后对查尔酮结构，氮杂环衍生物进行了进一步修饰，然后进行了评估，并报道了其对测试菌株的有效活性。进行了初步的对接研究，以探索目标分子与结合位点之间的相互作用。