Chinese Journal of Organic Chemistry >
Design, Synthesis and Bioactivity of Chalcone Derivative Containing Quinazolinone
Received date: 2023-04-25
Revised date: 2023-05-29
Online published: 2023-06-07
Supported by
National Natural Science Foundation of China(32072446); Science Fund of Guizhou Province(20192452)
Twenty-five chalcone derivatives containing quinazolinone were designed and synthesized. The results of antiviral biological experiments showed that (E)-3-(4-chlorophenyl)-6-fluoro-2-((2-(4-(3-(4-methoxyphenyl)acryloyl)phenoxy)ethyl)- thio)quinazolin-4(3H)-one (Z12) had a good inhibitory activity against tobacco mosaic virus (TMV), and the EC50 values of treatment and protection were 94.3 and 98.8 μg/mL, respectively, which were better than those of ningamycin (NNM, 216.1 and 189.6 μg/mL). The results of transmission electron microscope showed that Z12 broke TMV virus particles and formed rod structures of different lengths. The results of microscale thermophoresis experiment (MST) showed that the Kd value of Z12 binding to tobacco mosaic virus coat protein (TMV-CP) was (0.033±0.014) μmol/L. The Kd value of Z12 was better than that of ningnanmycin [(0.106±0.024) μmol/L], which indicated that Z12 had stronger binding ability to TMV-CP. The antibacterial test results showed that some compounds showed excellent activity against Xanthomonas oryzae pv. Oryzae (Xoo) and Xanthomonas axonopodis pv.Citri (Xac), among which ((E)-2-((2-(4-(3-(4-bromophenyl)acryloyl)phenoxy)ethyl)thio)-3- (4-chlorophenyl)-6-nitroquinazolin-4(3H)-one (Z25) showed the best activity against Xoo. The EC50 value of Xoo was 19.5 μg/mL, which was better than those of bismerthiazol (77.1 μg/mL) and thiodiazole copper (95.9 μg/mL). The results of scanning electron microscope showed that the cell membrane of Xoo was shriveled and deformed after Z25 treatment. The experimental results showed that chalcone derivatives containing quinazolinone were potential antiviral and antibacterial drugs.
Key words： quinazolinone; chalcone; organic synthesis; antibacterial; antiviral
Ran Zhou , Chunmei Yuan , Tao Zhang , Piao Mao , Yi Liu , Kaini Meng , Hui Xin , Wei Xue . Design, Synthesis and Bioactivity of Chalcone Derivative Containing Quinazolinone[J]. Chinese Journal of Organic Chemistry, 2023 , 43(9) : 3196 -3209 . DOI: 10.6023/cjoc202301020
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