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Abstract
To find new lead compounds with high antifungal activity, a series of new thiourea derivatives containing 1,3,4-thiadiazole and thioether skeleton was designed via linking the active sub-structures. The target compounds were prepared via three steps from the commercially available thiosemicarbazide. Their structures were characterized by means of HRMS, 1H NMR, 13C NMR and IR spectroscopy. The preliminary results indicate that the title compounds show various antifungal activity against the tested fungi. Compounds 4c, 4g, 4h, 4k, 4n, 4o, 4p, 4q and 4r display excellent antifungal activities against one or more tested fungi with inhibitory efficiencies of 90%―100% at 200 μg/mL. Especially, compound 4o shows the best inhibitory effect against Curvularia lunata, Cotton Fusarium Wilt, P. P. var nicotianae and Fusarium spp. with the EC50 values of 28.12, 30.41, 15.2 and 6.22 μg/mL, respectively, which are even superior to those of triadimefon(98.73, 96.58, 105.37 and 102.18 μg/mL). The preliminary structure-activity relationship indicates that allyl and aromatic groups are favorable to their antifungal activities.
Keywords
Thiourea
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2-Amino-5-alkylthio-1,3,4-thiadiazole
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Antifungal activity
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Caixia Wang, Hailong Song, Weiqun Liu, Cuilian Xu.
Design, synthesis and antifungal activity of novel thioureas containing 1,3,4-thiadiazole and thioether skeleton.
Chemical Research in Chinese Universities, 2016, 32(4): 615-620 DOI:10.1007/s40242-016-6023-8
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