1-(4-fluorophenyl)-3-(naphthalen-1-yl)-2-propen-1-one | 28081-22-3

• 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-1-yl)-2-propen-1-one
• 英文别名: 1-(4-fluorophenyl)-3-naphthalen-1-ylprop-2-en-1-one
• CAS: 28081-22-3
• 化学式: C₁₉H₁₃FO
• 分子量: 276.31
• InChiKey: VSYDYSJJUIIIPF-UHFFFAOYSA-N

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：

  1-(4-fluorophenyl)-3-(naphthalen-1-yl)-2-propen-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-1-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one
  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 、 1-萘甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以40.7%的产率得到1-(4-fluorophenyl)-3-(naphthalen-1-yl)-2-propen-1-one
  参考文献：
  名称：

  萘-查耳酮衍生物的合成及生物学作用

  摘要：

  本文合成了21种萘-查耳酮衍生物，并对其生物学效果进行了评价。结果表明，在强制游泳试验中，化合物2a–2u在30 mg / kg时显示出明显的抗抑郁活性。化合物2h，2o，2t和2u在30 mg / kg的强迫游泳试验和尾部悬吊试验中表现出良好的抗抑郁作用。化合物2h，2o，2t和2u在小鼠的野外试验中对运动能力没有影响。此外，化合物2o的最抗抑郁活性可能是由中枢神经系统中5-羟色胺和去甲肾上腺素水平升高介导的。化合物2a–2u在30 mg / kg时也显示出镇痛和抗炎作用。

  DOI：

  10.1007/s00044-020-02525-4

文献信息

• Thermodynamic and Acoustical study of 1-(4-Fluorophenyl)-3-(napthalen-1-yl)-2-propen-1-one
  作者：Balthikumeru Padmayya Sowmya

  DOI：10.13005/ojc/380123

  日期：2022.2.28

  The various concentrations (ranging from 0.01M to 0.1 M) of synthesized 1-(4-fluorophenyl)-3-(napthalen-1-yl)-2-propen-1-one1 (4FNP) solutions in DMF were prepared. Density (ρ), viscosity (η) and ultrasonic velocity (U) measurements of pure solvent and solutions were carried out at 288.15 K, 293.15 K, 298.15 K and 303.15 K. The observed values of ρ, η and U were found at 298.15K in the range of 944.50-954.25 kg.m-3, 0.8440 x10-3-1.4195 x10-3 Nm-2s and 1454-1513 ms-1 respectively. The values of η and U decreased with increase of temperature, reveals the weakening of intermolecular forces between the molecules at higher temparature. Calculated thermodynamic parameters such as free volume, Gibbs free energy and internal pressures were interpreted in terms solute-solvent interaction. Increase of Gibbs free energy with increase of concentration clearly indicates the strong interaction between solvent and solute molecules. Decrease of free volume with increase in mole fraction gives evidence of strong intermolecular interaction in solution. Positive excess values of internal pressure represent the presence of dispersive forces between molecules.