RESUMO
Quinazoline and/or chalcones derivatives are important targets in several areas of chemical sciences, mainly, in the medicinal chemistry and pharmaceutical research. The purpose of this review was to systematize the information available in the literature, including patents, regarding the benefits, exerted by the combination of these two pharmacophores into single molecules. These hybrid compounds can exhibit different biological activities, causing a synergistic or a new effect, compared to the individuals. The variability of biological activities includes anticancer, anti-Alzheimer, antiviral and antimicrobial activities, among others. Additionally, synthetic methodologies to prepare the different molecular architectures were discussed based on their similarities. The increasing number of publications indicates the importance of molecular hybridization in the field of drug discovery.
Assuntos
Anti-Infecciosos/química , Antineoplásicos/química , Chalconas/química , Quinazolinas/química , Quinazolinonas/química , Anti-Infecciosos/síntese química , Anti-Infecciosos/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Bactérias/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Fungos/efeitos dos fármacos , Humanos , Vírus/efeitos dos fármacosRESUMO
Singlet oxygen ene reactions produce 2-(tert-butyl)-4a-hydroperoxy-3-methyl-2,4a, 5,6,7,8-hexahydroquinazolin-4(3H)-one quantitatively during diffusion crystallization of 2-(tert-butyl)-3-methyl-2,3,5,6,7,8-hexahydroquinazolin-4(1H)-one in n-hexane/CH2Cl2 solvent mixture. To confirm this photo-oxidation, a 1H-NMR study in CDCl3 was performed with exposure to ambient conditions (light and oxygen), with neither additional reactants nor catalysts. A theoretical study at the B3LyP/6311++G** level using the QST2 method of locating transition states suggests a two-step mechanism where the intermediate, which unexpectedly did not come from the peroxide intermediate, has a low activation energy.