2-(2-(trifluoromethyl)phenyl)-3-hydroxy-4H-chromen-4-one | 1429665-34-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(2-(trifluoromethyl)phenyl)-3-hydroxy-4H-chromen-4-one
• 英文别名: 3-hydroxy-2’-trifluoromethylflavone
• CAS: 1429665-34-8
• 化学式: C₁₆H₉F₃O₃
• 分子量: 306.241
• InChiKey: ZQFGWPYSAFMQTE-UHFFFAOYSA-N

物化性质

• 沸点：
  402.7±45.0 °C(predicted)
• 密度：
  1.473±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2-(trifluoromethyl)phenyl)-3-hydroxy-4H-chromen-4-one 、 1-溴-2-丁炔 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到3-(but-2-ynyloxy)-2-(2-(trifluoromethyl)phenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Metal-Catalyzed Cascade Rearrangements of 3-Alkynyl Flavone Ethers

  摘要：

  Metal-mediated rearrangements of 3-alkynyl flavone ethers are reported. The overall process involves 5-endo enyne cyclization to a platinum. containing spiro-oxocarbenium intermediate which may be trapped with methanol to produce spirodihydrofurans or further rearranged to afford either allenyl chromanediones or benzofuranones.

  DOI：

  10.1021/ol400631b
• 作为产物：
  描述：

  1-(2-Hydroxyphenyl)-3-(2-(trifluoromethyl)phenyl)prop-2-en-1-one 在 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 2-(2-(trifluoromethyl)phenyl)-3-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies

  摘要：

  To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened forin vitroagainst mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis,H-1-,C-13-NMR) and mass spectrometry (EI-MS). The structure of compound15was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibioticsi.e.Cefixime and Clotrimazole. Amongst the series, the compounds2, 4, 5, 6, 7, 10, 11, 14and22exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound2(IC50= 0.280 +/- 0.010 mu g/ml) was found almost sixfold and derivative5(IC50= 0.230 +/- 0.020 mu g/ml) about sevenfold more active as compared to standard Kojic acid (IC50=1.79 +/- 0.6 mu g/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma

  DOI：

  10.1080/07391102.2020.1805364