Study On The Synthesis And Biological Activity Of D-Glucosamine Derivatives

D-glucosamine is a kind of important minosaccharide, which possesses extensive bioactivities including antibacterial, insecticidal and plant growth-regulating activities. Research aimed at synthesising new D-glucosamine derivatives has continued in recent years.A series of 2-aryloxyacetylamino-2-deoxy-D-glucoses have been synthesized by acylation of D-glucosamine with aryloxyacetyl chlorides. The effect of several factors, such as solvent variety, reaction time, reaction temperature, ratio of reactants was investigated. The process parameters were optimized. All of their plant growth-regulating activities were tested. The results show that those compounds bearing chlorine atom at para position of benzene ring have notable inhibiting activities against cotyledon rootage of cucumber which are comparable with that of 2,4-dichlorophenoxyacetic acid(2,4-D).In order to improve the solubility of 2-aryloxyacetylamino- 2-deoxy-D-glucoses, methyl 2-deoxy-2-phenoxyacetyl-D-glucosides with better solubility were synthesized by H₂SO₄-SiO₂ catalyst in methanol in yields 85-97%.In addition, thiadiazole derivative has been introduced into D-glucosamine. A new compound, 2-(4'-methyl-1',2',3'-thiadiazole- 5'-acetyl) amino-2-deoxy-D-glucose, has been obtained in yield 54 %. Compounds structures were confirmed by 1H NMR,MS and IR, melting points of all new compounds were determined.