Design, Synthesis and Bioactivity of Novel Glycosylthiadiazole Derivatives

Molecules

Guanghui Zong²  Hanqing Zhao²  Rui Jiang²  Jianjun Zhang²  Xiaomei Liang²  Baoju Li¹  Yanxia Shi¹ 

[1] Institute of Vegetables and Flowers, Chinese Academy of Agricultural Sciences, Beijing 100081, China;Department of Applied Chemistry, China Agricultural University, Beijing 100193, China

关键词: 1;    3;    4-thiadiazole;    carbohydrates;    synthesis;    fungicidal activity;   

DOI  :  10.3390/molecules19067832

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.