379228-58-7 | 5,7-DIFLUOROQUINAZOLIN-4(3H)-ONE

CAS:379228-58-7 | 5,7-DIFLUOROQUINAZOLIN-4(3H)-ONE,Description

5,7-Difluoroquinazolin-4(3H)-one (DFQ) is a heterocyclic compound with the molecular formula C6H3F2N3O. It is a member of the quinazoline family, which has been widely studied for its potential applications in medicinal chemistry and drug discovery. DFQ has been found to possess a variety of biological activities, including anti-inflammatory, anti-tumor, antifungal, and antiviral properties. In addition, DFQ has been used in the synthesis of various pharmaceuticals and agrochemicals. 
 

Scientific Research Applications

Photophysical and Electrochemical Properties

Photophysical and Electrochemical Studies : 5,7-difluoroquinazolin-4(3H)-one derivatives have been studied for their optical and electrochemical properties, which include UV-Vis absorption, fluorescence spectroscopy, life time, and cyclic voltammetry measurements. Quantum yield and solvent effects were investigated, and Density Functional Theory (DFT) computations supported the experimental findings. These derivatives exhibited moderate to good anticancer activities, as evaluated at the National Cancer Institute, NIH, Bethesda, USA (Kamble et al., 2017).

Synthesis Methods and Catalysis

Gallium(III) Triflate-Catalyzed Synthesis : A method for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones has been established using gallium(III) triflate as a catalyst. This one-pot reaction utilizes isatoic anhydride, ammonium acetate (or amines), and aldehydes, yielding products with good to excellent yields and high selectivity (Chen et al., 2008).

Eco-Friendly Synthesis in Ionic Liquids : An eco-friendly approach has been developed for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones in ionic liquids or ionic liquid-water solvent systems without the need for an additional catalyst. The cyclocondensation of anthranilamides and aldehydes or a one-pot three-component cyclocondensation of isatoic anhydrides, ammonium acetate, and aldehydes in these solvent systems has shown to produce high yields (Chen et al., 2007).

Synthesis Promoted by Low-Valent Titanium : Low-valent titanium reagent (TiCl4-Zn system) has been used to promote the synthesis of dihydroquinazolin-4(3H)-ones from o-nitrobenzamides and aromatic aldehydes or cyclones. The method provides moderate to high yields and offers advantages such as easy accessibility to starting materials and convenient manipulation (Da, 2004).

Biological Activity and Applications

Anticancer Activity : Several derivatives of 5,7-difluoroquinazolin-4(3H)-one have shown promising anticancer activities, with moderate to good results in inhibiting cancer cell growth. The compounds were characterized by various analytical techniques and evaluated for their anticancer activity at the National Cancer Institute, NIH, Bethesda, USA (Kamble et al., 2017).

Inhibitors of Plasmepsins in Malaria : 2-Aminoquinazolin-4(3H)-ones were identified as a novel class of malaria digestive vacuole plasmepsin inhibitors. These compounds exhibit activity against digestive Plms I, II, and IV, showing potential as leads for future antimalarial agents. The compounds also displayed cell-based growth inhibition of Plasmodium falciparum, suggesting their utility in malaria treatment (Rasina et al., 2016).

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