title: Design, synthesis and bioactivity of novel glycosylthiadiazole derivatives.
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.
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors: Guanghui
authors: G
authors: Zong
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors: Hanqing
authors: H
authors: Zhao
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors: Rui
authors: R
authors: Jiang
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China. zhangjianjun@cau.edu.cn.
authors: Jianjun
authors: J
authors: Zhang
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors: Xiaomei
authors: X
authors: Liang
authors: Institute of Vegetables and Flowers, Chinese Academy of Agricultural Sciences, Beijing 100081, China.
authors: Baoju
authors: B
authors: Li
authors: Institute of Vegetables and Flowers, Chinese Academy of Agricultural Sciences, Beijing 100081, China. shiyanxia@caas.cn.
authors: Yanxia
authors: Y
authors: Shi
authors: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors: Daoquan
authors: D
authors: Wang
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001203:Ascomycota / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects / Q000201:enzymology; D005658:Fungi / Q000187:drug effects*; D005945:Glutamine-Fructose-6-Phosphate Transaminase (Isomerizing) / Q000037:antagonists & inhibitors*; D006375:Helminthosporium / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D003904:Mitosporic Fungi / Q000187:drug effects; D015394:Molecular Structure; D009570:Nitriles / Q000494:pharmacology; D010838:Phytophthora / Q000187:drug effects; D012232:Rhizoctonia / Q000187:drug effects; D013329:Structure-Activity Relationship; D013830:Thiadiazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D020172:Verticillium / Q000187:drug effects
chemical_list: D000935:Antifungal Agents; D009570:Nitriles; D013830:Thiadiazoles; D005945:Glutamine-Fructose-6-Phosphate Transaminase (Isomerizing); C005806:tetrachloroisophthalonitrile