Synthesis of novel 2-phenylsulfonylhydrazono-3-(2',3',4',6'-tetra-O-acetyl-beta-d-glucopyranosyl)thiazolidine-4-ones from thiosemicarbazide precursors.
To develop novel biologically active organic compounds possessing a sugar moiety, a series of 2-phenylsulfonylhydrazono-3-(2',3',4',6'-tetra-O-acetyl-beta-d-glucopyranosyl)thiazolidine-4-one were synthesized via reaction of the thiosemicarbazide with ethyl bromoacetate. Their chemical structures were characterized by (1)H and (13)C NMR spectroscopy, elemental analysis and MS. The bioassay results indicated that some of these compound exhibit moderate fungicidal and herbicidal activities. Furthermore, the effect of various solvents at reflux temperature on the reactions of ethyl bromoacetate with the related thiosemicarbazides was investigated.
Li
Yu Xin
YX
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China.
Wang
Su Hua
SH
Li
Zheng Ming
ZM
Su
Na
N
Zhao
Wei Guang
WG
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002240:Carbohydrate Sequence; D006540:Herbicides / Q000138:chemical synthesis* / Q000737:chemistry; D012663:Semicarbazides / Q000138:chemical synthesis* / Q000737:chemistry*; D013863:Thioglucosides / Q000737:chemistry*
D000935:Antifungal Agents; D006540:Herbicides; D012663:Semicarbazides; D013863:Thioglucosides; C005151:thiosemicarbazide