Synthesis and bioactivity of novel sulfone derivatives containing 2,4-dichlorophenyl substituted 1,3,4-oxadiazole/thiadiazole moiety as chitinase inhibitors |
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Authors: | Weiming Xu Song Yang Pinaki Bhadury Jiang He Ming He Lili Gao Deyu Hu Baoan Song |
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Institution: | State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China |
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Abstract: | The paper reported the synthesis and antifungal properties and mechanism of action of a series of 2-substituted methylthio-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole/thiadiazole and their corresponding sulfones. The preliminary biological test showed these compounds exhibit moderate to good antifungal activity. Particularly, the compounds 7g and 7c inhibited mycelia growth by approximately 50% (EC50) at 2.6–59.2 μg/mL and 17.2–54.4 μg/mL respectively against nine kinds of fungi. The extent of inhibition induced by 7c on Rhizoctonia solani and underlying mechanism of action were studied in vitro. Docking simulation was performed to position selected compounds into the active site of family 18 chitinases. Variation in d-GlcNAc content and chitinase activity indicated that 7c can act as chitinase inhibitor for controlling fungal pathogens in plants. |
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Keywords: | Abbreviations: 1H NMR 1H nuclear magnetic resonance 13C NMR 13C nuclear magnetic resonance G zeae Gibberella zeae C mandshurica Cytospora mandshurica F oxysporum Fusarium oxysporum P infestans Phytophthora infestans R solani Rhizoctonia solani T cucumeris Thanatephorus cucumeris C gloeosporioides Colletotrichum gloeosporioides B cinerea Botrytis cinerea S sclerotiorum Sclerotinia sclerotiorum d-GlcNAc content" target="_blank">d-GlcNAc content d-acetylglucosamine" target="_blank">d-acetylglucosamine |
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