Synthesis, Antiviral Activity, and Mechanisms of Purine Nucleoside Derivatives Containing a Sulfonamide Moiety

• Published in: Journal of agricultural and food chemistry 2019-08, Vol.67 (31), p.8459-8467
• Main Authors: He, Fangcheng, Shi, Jing, Wang, Yanju, Wang, Shaobo, Chen, Jixiang, Gan, Xiuhai, Song, Baoan, Hu, Deyu
• Format: Article
• Language: English
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/acs.jafc.9b02681

Novel purine nucleoside derivatives containing a sulfonamide moiety were prepared, as well as their antiviral activities against potato virus Y (PVY), cucumber mosaic virus (CMV), and tobacco mosaic virus (TMV) were evaluated. The antiviral mechanisms of the compounds were investigated. Results showed that most of the compounds had good antiviral activities. Compound 5 at 500 μg/mL exhibited excellent curative and protective activities of 52.5% and 60.0% and of 52.0% and 60.2% for PVY and CMV, respectively, which are higher than those of ningnanmycin (48.1%, 49.6%; 45.3%, 47.7%), ribavirin (38.3%, 48.2%; 40.8%, 45.5%), and chitosan oligosaccharide (32.5%, 33.8%; 35.1%, 34.6%). Moreover, compound 5 displayed good inactivating activity against TMV, with an EC50 value of 48.8 μg/mL, which is better than that of ningnanmycin (84.7 μg/mL), ribavirin (150.4 μg/mL), and chitosan oligosaccharide (521.3 μg/mL). The excellent antiviral activity of compound 5 is related to its immune induction effect which can regulate the physiological and biochemical processes in plants, including defense-related enzyme activities, defense-related genes, and photosynthesis-related proteins. These results indicate that purine nucleoside derivatives containing a sulfonamide moiety are worthy of further research and development as new antiviral agents.