Design, synthesis and bioactivity of novel glycosylthiadiazole derivatives.

Guanghui Zong,Hanqing Zhao,Jianjun Zhang,Baoju Li,Yanxia Shi,Daoquan Wang,Rui Jiang,Xiaomei Liang

doi:10.3390/molecules19067832

Abstract

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.

Highlights

Carbohydrates play an important role in the field of pesticide investigation, and many natural carbohydrate products used as pesticides have shown great vitality
Encouraged by the successes of the developed commercial pesticides based on natural carbohydrates, pesticide chemists have paid considerable attention to the design, synthesis and activity evaluation of novel carbohydratecontaining compounds as potential pesticides, finding that heterocyclic compounds modified by carbohydrates exhibit excellent biological activities [10,11,12,13]
It is well established that 1,3,4-thiadiazole and their derivatives exhibit a broad spectrum of biological activities in research on drugs with anticancer [14], antimicrobial [15], antituberculosis [16], anticonvulsant [17], or anti-inflammatory activities [18,19] and in pesticide research such as antifungal [20,21], insecticidal [22], herbicidal [23] and plant growth regulating agents [24]

Summary

Introduction

Carbohydrates play an important role in the field of pesticide investigation, and many natural carbohydrate products used as pesticides have shown great vitality. Many natural products containing glycosyl residues in their structures, such as the derivatives of avermecin and spinosad, are well known green pesticides and widely used in the control of many kinds of pests, taking the advantage of excellent bioactivities, good environment compatibility and structure variability [6,7,8,9]. Encouraged by the successes of the developed commercial pesticides based on natural carbohydrates, pesticide chemists have paid considerable attention to the design, synthesis and activity evaluation of novel carbohydratecontaining compounds as potential pesticides, finding that heterocyclic compounds modified by carbohydrates exhibit excellent biological activities [10,11,12,13]. An interest in developing novel bioactive agents with low toxicities and an acceptable impact on the environment is increasing. One way to reach this goal is to modify the parent 1,3,4-thiadiazole structure

Methods

Results

Conclusion