Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (9): 3196-3209.DOI: 10.6023/cjoc202301020 Previous Articles     Next Articles


周然, 袁春梅, 张桃, 毛飘, 刘燚, 孟开妮, 幸惠, 薛伟*()   

  1. 贵州大学绿色农药全国重点实验室 绿色农药与生物工程教育部重点实验室 贵阳 550025
  • 收稿日期:2023-04-25 修回日期:2023-05-29 发布日期:2023-06-06
  • 基金资助:
    国家自然科学基金(32072446); 贵州省科学基金(20192452)

Design, Synthesis and Bioactivity of Chalcone Derivative Containing Quinazolinone

Ran Zhou, Chunmei Yuan, Tao Zhang, Piao Mao, Yi Liu, Kaini Meng, Hui Xin, Wei Xue()   

  1. National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025
  • Received:2023-04-25 Revised:2023-05-29 Published:2023-06-06
  • Contact: E-mail:
  • 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