Synthesis, anti-tobacco mosaic virus and cucumber mosaic virus activity, and 3D-QSAR study of novel 1,4-pentadien-3-one derivatives containing 4-thioquinazoline moiety

European Journal of Medicinal Chemistry
Chengwen LongBaoan Song

Abstract

A series of novel 1,4-pentadien-3-one derivatives containing 4-thioquinazoline moiety were designed and synthesized. Antiviral bioassay results indicated that most of the title compounds exhibited excellent antiviral activities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) in vivo. Among the title compounds, 7j exhibited the best curative activity against TMV, with a half-maximal effective concentration (EC50) value of 213.5 μg/mL, which was better than that of ningnanmycin (270.9 μg/mL). Meanwhile, 7a showed remarkable protection activity against TMV and curative activity against CMV, with EC50 values of 124.3 and 365.5 μg/mL, respectively, which were superior to those of ningnanmycin (195.1 and 404.9 μg/mL, respectively). Comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) models were generated on the basis of the curative activities against TMV and exhibited good predictive abilities with cross-validated q(2) and non-cross-validated r(2) values for CoMFA and CoMSIA of 0.548, 0.647 and 0.994, 0.993, respectively. These results provided a practical tool for guiding the design and synthesis of novel and more potent 1,4-pentadien-3-one derivatives contain...Continue Reading

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Citations

Apr 22, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Lu YuDeyu Hu
Dec 19, 2018·International Journal of Molecular Sciences·Limin YinBaoan Song
Sep 3, 2020·Journal of Pesticide Science·Xu TangWei Xue
Jul 28, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Dorota G PiotrowskaMagdalena Grabkowska-Drużyc
Oct 23, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Zai-Bo YangYin-Ju He
Dec 6, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Qing-Wei TanQi-Jian Chen
Jul 25, 2019·Journal of Agricultural and Food Chemistry·Fangcheng HeDeyu Hu

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