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Molecules 2014, 19(6), 7832-7849;

Design, Synthesis and Bioactivity of Novel Glycosylthiadiazole Derivatives

Department of Applied Chemistry, China Agricultural University, Beijing 100193, China
Department of Fundamental Science, Beijing University of Agriculture, Beijing 102206, China
Institute of Vegetables and Flowers, Chinese Academy of Agricultural Sciences, Beijing 100081, China
The authors contributed equally to this paper.
Authors to whom correspondence should be addressed.
Received: 21 April 2014 / Revised: 4 June 2014 / Accepted: 5 June 2014 / Published: 11 June 2014
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A series of novel glycosylthiadiazole derivatives, namely 2-phenylamino-5-glycosyl-1,3,4-thiadiazoles, were designed and synthesized by condensation between sugar aldehydes A/B and substituted thiosemicarbazide C followed by oxidative cyclization by treating with manganese dioxide. The original fungicidal activities results showed that some title compounds exhibited excellent fungicidal activities against Sclerotinia sclerotiorum (Lib.) de Bary and Pyricularia oryzae Cav, especially compounds F-5 and G-8 which displayed better fungicidal activities than the commercial fungicide chlorothalonil. At the same time, the preliminary studies based on the Elson-Morgan method indicated that many compounds exhibited some inhibitory activity toward glucosamine-6-phosphate synthase (GlmS). The structure-activity relationships (SAR) are discussed in terms of the effects of the substituents on both the benzene and the sugar ring. View Full-Text
Keywords: 1,3,4-thiadiazole; carbohydrates; synthesis; fungicidal activity 1,3,4-thiadiazole; carbohydrates; synthesis; fungicidal activity

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Zong, G.; Zhao, H.; Jiang, R.; Zhang, J.; Liang, X.; Li, B.; Shi, Y.; Wang, D. Design, Synthesis and Bioactivity of Novel Glycosylthiadiazole Derivatives. Molecules 2014, 19, 7832-7849.

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