Facile Synthesis of Novel Vanillin Derivatives Incorporating a Bis(2-hydroxyethyl)dithhioacetal Moiety as Antiviral Agents

A series of vanillin derivatives incorporating a bis­(2-hydroxyethyl)­dithioacetal moiety was designed and synthesized via a facile method. A plausible reaction pathway was proposed and verified by computational studies. Bioassay results demonstrated that target compounds possessed good to excellent...

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Veröffentlicht in:Journal of agricultural and food chemistry 2017-06, Vol.65 (23), p.4582-4588
Hauptverfasser: Zhang, Jian, Zhao, Lei, Zhu, Chun, Wu, Zengxue, Zhang, Guoping, Gan, Xiuhai, Liu, Dengyue, Pan, Jianke, Hu, Deyu, Song, Baoan
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Sprache:eng
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Zusammenfassung:A series of vanillin derivatives incorporating a bis­(2-hydroxyethyl)­dithioacetal moiety was designed and synthesized via a facile method. A plausible reaction pathway was proposed and verified by computational studies. Bioassay results demonstrated that target compounds possessed good to excellent activities against potato virus Y (PVY) and cucumber mosaic virus (CMV), of which, compound 6f incorporating a bis­(2-hydroxyethyl)­dithioacetal moiety, exhibited the best curative and protection activities against PVY and CMV in vivo, with 50% effective concentration values of 217.6, 205.7 μg/mL and 206.3, 186.2 μg/mL, respectively, better than those of ribavirin (848.0, 808.1 μg/mL and 858.2, 766.5 μg/mL, respectively), dufulin (462.6, 454.8 μg/mL and 471.2, 465.4 μg/mL, respectively), and ningnanmycin (440.5, 425.3 μg/mL and 426.1, 405.3 μg/mL, respectively). Current studies provide support for the application of vanillin derivatives incorporating bis­(2-hydroxyethyl)­dithioacetal as new antiviral agents.
ISSN:0021-8561
1520-5118
DOI:10.1021/acs.jafc.7b01035