1-(4-fluorophenyl)-3-naphthalen-2-ylprop-2-en-1-one | 1242261-37-5

• 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: 1-(4-fluorophenyl)-3-naphthalen-2-ylprop-2-en-1-one
• CAS: 1242261-37-5
• 化学式: C₁₉H₁₃FO
• 分子量: 276.31
• InChiKey: KXEDVEHGTNJKHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenyl)-3-naphthalen-2-ylprop-2-en-1-one 在 sodium acetate 、 乙酸酐 、 potassium hydroxide 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 12.0h， 生成 2-(3-(4-fluorophenyl)-5-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-phenylthiazole
  参考文献：
  名称：

  Synthesis and biological evaluation of compounds which contain pyrazole, thiazole and naphthalene ring as antitumor agents

  摘要：

  A series of compounds which contain pyrazole, thiazole and naphthalene ring (1a-7a, 1b-7b, 1c-7c, 1d-7d) were firstly synthesized and their anti-proliferative activity, EGFR inhibitory activity, cytotoxicity and inhibition to Hela cell migration were evaluated. Compound 2-(3-(3,4-dimethylphenyl)-5-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl) thiazol-4(5H)-one (7d) displayed the most potent inhibitory activity (IC50 = 0.86 mu M for Hela and IC50 = 0.12 mu M for EGFR). Structure-activity relationship (SAR) analysis showed that the anti-proliferative activity was affected by A-ring-substituent (-OCH3 > -CH3 > -H > -Br > -Cl > -F). Docking simulation of compound 7d into EGFR active site showed that naphthalene ring of 7d with LYS721 formed two p-pi bonds, which enhanced antitumor activity. Therefore, compound 7d may be developed as a potential antitumor agent. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.072
• 作为产物：
  描述：

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

  含二氢吡唑作为潜在EGFR激酶抑制剂的苯并肼衍生物的设计，合成和生物学评估。

  摘要：

  已经合成了一系列含有二氢吡唑的新型苯并酰肼衍生物作为潜在的表皮生长因子受体（EGFR）激酶抑制剂，并评估了它们作为潜在的抗增殖剂的生物学活性。在这些化合物中，化合物H20对四种癌细胞系变体（A549，MCF-7，HeLa，HepG2）表现出最强的抗增殖活性，IC50值分别为0.46、0.29、0.15和0.21μM，显示出最强的EGFR抑制作用活性（EGFR的IC50 = 0.08μM）。为了预测这些苯并酰肼衍生物的生物活性和活性关系（SAR），进行了分子模型模拟研究。这些结果表明，化合物H20可能是有前途的抗癌药。

  DOI：

  10.3390/molecules21081012

文献信息

• Metal-free C(sp3)–H bond activation: first synthesis of diaryl-pyridinium-azaarene-butenolate zwitterionic salts on chalcones
  作者：Atul Kumar、Lalit Prakash Gupta、Mukesh Kumar

  DOI：10.1039/c3ra42761g

  日期：——

  An efficient route for the synthesis of diaryl-pyridinium-azaarene-butenolate zwitterionic derivatives via metal-free, iodine-mediated C(sp3)–H bond activation of alkyl-azaarenes on addition to the α,β-unsaturated carbonyls has been reported.

  报道了一种高效路线，用于通过无金属、碘介导的C(sp3)–H键活化，合成二芳基吡啶鎓-氮杂烯-丁烯酸酯的两性离子衍生物，反应是在烷基氮杂芳烃与α,β-不饱和羰基化合物反应时进行的。
• Palladacycle-Catalyzed Asymmetric Hydrophosphination of Enones for Synthesis of C*- and P*-Chiral Tertiary Phosphines
  作者：Yinhua Huang、Sumod A. Pullarkat、Yongxin Li、Pak-Hing Leung

  DOI：10.1021/ic202472f

  日期：2012.2.20

  the synthesis of C*- and P*-chiral tertiary phosphines has been developed. When Ph2PH was employed as the hydrophosphinating reagent, a series of C*-chiral tertiary phosphines were synthesized (C*–P bond formation) in high yields with excellent enantioselectivities, and a single recrystallization provides access to their enantiomerically pure forms. When racemic secondary phosphines rac-R3(R4)PH were

  已经开发了由palladacycles催化的烯酮的高反应性和立体选择性氢磷酸化反应，用于合成C *-和P *-手性叔膦。当使用Ph 2 PH作为加氢膦酸酯化试剂时，以高收率和优异的对映选择性合成了一系列C *-手性叔膦（C * -P键形成），并且一次重结晶即可获得其对映体纯形式。当外消旋仲膦rac -R 3（R 4）PH被利用，以高产率产生了具有C *-和P *手性中心的一系列叔膦（C * -P *键形成），具有良好的非对映和对映选择性。已经揭示了催化循环中涉及的立体电子因素。
• Comparative DFT Computational Studies with Experimental Investigations for Novel Synthesized Fluorescent Pyrazoline Derivatives
  作者：Ahmad Saed Salim、Adel S. Girgis、Altaf H. Basta、Houssni El-saied、Mohamed A. Mohamed、Ahmad H. Bedair

  DOI：10.1007/s10895-018-2254-z

  日期：2018.7

  A novel series of pyrazoline derivatives were synthesized and their spectral properties were characterized via FT-IR, 1H, and 13C NMR. The electronic transitions and fluorescence properties were tracked via UV-Vis and emission spectrometry. The density functional theory (DFT) calculations have been also computed to get spot onto the geometry, electronic transitions and spectroscopic properties theoretically

  合成了一系列新型的吡唑啉衍生物，并通过FT-IR，1 H和13 C NMR表征了其光谱性质。通过UV-Vis和发射光谱法追踪电子跃迁和荧光性质。密度泛函理论（DFT）的计算也已经计算出来，从理论上可以发现几何形状，电子跃迁和光谱性质，并与遇到的实验进行了比较。此外，计算了具有高荧光量子产率的新型候选吡唑啉衍生物的偶极矩，优化能量，HOMO-LUMO能量和带隙。
• Sulfonamide derivatives containing dihydropyrazole moieties selectively and potently inhibit MMP-2/MMP-9: Design, synthesis, inhibitory activity and 3D-QSAR analysis
  作者：Xiao-Qiang Yan、Zhong-Chang Wang、Zhen Li、Peng-Fei Wang、Han-Yue Qiu、Long-Wang Chen、Xiao-Yuan Lu、Peng-Cheng Lv、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2015.08.026

  日期：2015.10

  New series of sulfonamide derivatives containing a dihydropyrazole moieties inhibitors of MMP-2/MMP-9 were discovered using structure-based drug design. Synthesis, antitumor activity, structure-activity relationship and optimization of physicochemical properties were described. In vitro the bioassay results revealed that most target compounds showed potent inhibitory activity in the enzymatic and cellular assays. Among the compounds, compound 3i exhibited the most potent inhibitory activity with IC50 values of 0.21 mu M inhibiting MMP-2 and 1.87 mu M inhibiting MMP-9, comparable to the control positive compound CMT-1 (1.26 mu M, 2.52 mu M). Docking simulation was performed to position compound 3i into the MMP-2 active site to determine the probable binding pose. Docking simulation was further performed to position compound 3i into the MMP-2 active site to determine the probable binding model the 3D-QSAR models were built for reasonable design of MMP-2/MMP-9 inhibitors at present and in future. (C) 2015 Elsevier Ltd. All rights reserved.