以6-氯邻氨基苯甲酸为起始原料,与醋酐酰化关环制得6-氯-2-甲基嗯嗪-4-酮(1);1在80%水合肼中回流反应制得6-氯-2-甲基-3-氨基-4(3H)-喹唑啉酮(2);2与羟基芳醛反应合成了4种新型的6-氯4(3H)-喹唑啉酮类Schiff碱(4a-4d),其结构经。HNMR,13C NMR,IR和元素分析表征。采用琼脂扩散法研究了4a~4d对金黄色葡萄球菌(A)、大肠杆菌(B)和枯草杆菌(C)的抑制活性。结果表明:用药浓度为300mg·mL-1时,4a-4d对A~C均有一定的抑制活性,其中6-氯-2-甲基-3-(5-甲基-2-羟基苯亚甲氨基)-4(3H)-喹唑啉酮(4c)抑菌活性最强,对A~C的抑菌圈直径分别为8.8mm,11.9mm和9.6mm。
6-Chlor-2-methyl-3,1-benzoxazin-4-one (1) was prepared by acylated cyclization of 6- chlor-anthranilic acid with acetic oxide. 3-Amino-6-chlor-2-methyl-4(3H)-quinazolinone (2) was obtained by refluxing reaction of 1 in 80% N2 H4 · H2 O. Four novel 6-chlor-4 (3H) -quinazolinone Schiff bases(4a - 4d) were synthesized by the reaction of 2 with hydroxyl arylamine. The structures were characterized by 1H NMR, 13C NMR, IR and elementary analysis. The preliminary antibacterial activities of 4a - 4d against Staphylococcus aureus (A), Escherichia coli (B) and Bacillus subtilis (C) were investigated by agar diffusion method. The results showed that 4a - 4d exhibited certain antibacterial activities with drug concentration of 300 mg · mL - 1 and 6-chlor-2-methyl-3- [ ( 5-methyl-2-hydroxyphenyl) methylene amimo ] -4 (3H) -quinazolinone (4c) was the best, which possessed 8.8 mm, 11.9 mm and 9.6 mm inbibition zone diameters against A - C, respectively.