| Quinazolinone is a type of compound with high biological activity. Twelve 3-alkylquinazolinones were synthesized by our group in 2005 and their bioactivities were evaluated. The results showed that some of the compounds demonstrated fungicidal activity against C. mandshurica.The paper focused on the discovey of high fungicial activity of new quinazolinones. Aromatic group and heterocycyclic moities were introduced into the structure of quinazolinone by our group. 20 title compounds were synthesized. Among which 10 new compounds were synthesized from gallic acid and the rest were synthesized from anthranilic acid. All structures were confirmed by 1H NMR, 13C NMR, IR and elemental analysis.At the same time, optimization for the synthesis of target compounds was carried out under several conditions, such as solvent-free, microwave irradiation and catalytic conditions, and their effect on the reaction was researched. Under optimal conditions, the p-toluenesulfonic acid catalyzed one-pot synthesis of quinazolin-4(3H)ones under solvent-free conditions, was confirmed as the most suitable under laboratory conditions. The best condition of synthesis was established with molar ratio of anthranilic acid : aromatic amines : triethyl ortho-formate meaning 1 :1.2 :1.2, catalytic dose of 5 percent, reaction temperature at 30±5℃. Compared with traditional synthetic methods, the presend method shortens the reaction time from the original 1 h to 15 min; improves the yield from the original 63.5 percent to 90.2 percent, and has the advantage of being environment-friendly.The results of biological activity test showed that the two target compounds possessed anti-TMV activities in vivo. Inhibitory activities of target H20 and Ningnanmycin were 42.6% and 49.3% at 500μg/mL respectively. In anti-fungal activity experiment, most compounds exhibited antifungal activities. Especially compound H19 showed 100% inhibitory activity against G. zeae, F. oxysporum and C. mandshurica at 500μg/mL. |
PDF Full Text Request