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Synthesis Of Glycosylaminoguanidine And Guanidinopyrazolylaldehyde Hydrazone

Posted on:2009-07-16Degree:MasterType:Thesis
Country:ChinaCandidate:Y W ZhaoFull Text:PDF
GTID:2121360245485469Subject:Organic Chemistry
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Aminoguanidines, the derivatives of guanidine, have always been the fields that the researchers are interesting of in biology and clinic physic, mainly because they show extraordinary officinal value when treating fatal illness, such as in the domain of clinic physic, they can be medicine of therapy and prevention against diabetic complications, show delay action against growing asthma, can improve acute respiration disconcerted syndrome, possess potent therapy for ravage and hemorrhage shock and show protective action of organ transplantation and brain function. In addition, aminoguanidine analog exhibit some activities such as anticancer, antibacterial, antivirus, anti-HIV-1 PR, anti-HIV-1 reverse transcriptase inhibitory activity as guanidine.Some pyrazole derivatives have been shown to exhibit biological activity such as anti-hyperglycemic, analgesic, anti-inflammatory, anti-pyretic, anti-bacterial, hypoglycemic, sedative-hypnotic activity and anticoagulant activity. Particularly, arylpyrazoles have inhibitory activity against non-nucleoside HIV-1 reverse transcriptase.In view of some characteristics of saccharide compounds, such as easily deliquescent, potent absorbent and potentially biodegradable, non-toxic, we designed and synthesized guanidine moieties incorporating with carbohydrate fragments as well as bioactive arylthiazole ring in an effort to enhance their biological activity and a series of desired glucosyl aminoguanidine compounds as well as corresponding guanylhydrazone derivatives were obtained.The structures of all the compounds synthesized were identified on the basis of IR, 1H NMR and MS spectra and elemental analysis. The biological activities test of representative target compounds showed that they possessed modest anti-HIV-1 PR and inhibitory activity against nitric oxide synthase.The major accomplishments of this work1. 2-Amino-4-arylthiazoles were refluxed with acetylated glucosylisothocyantes to prepare the glucosylthiourea. Sudsequent desulfurization of the resulting thiourea with mercuric chloride in presence of hydrazine gave glucosyl aminoguanidines which can be converted to corresponding guanylhydrazone derivatives by the condensation with substituted 4-formylpyrazole.2. Corresponding glycosyl aminothioureas were prepared from anhydrous hydrazine and acetylated glycosyl isothiocyanate, which reacted with substituted 4-formylpyrazole under 4? molecular sieve to give a series of N-glycosyl-N′-(1-phenyl-3-arylpyrazole- 4-yl)methyleneaminothioureas.The major innovations of this work1. We attempted to use 4? molecular sieve to improve the methods of preparation about glycosyl thioureas. Simultaneously, the compounds were detected by fluorescence spectrophotometer in order to discover novel fluorescence labeled derivative of sugar.2. A series of novel glycosyl aminoguanidine as well as corresponding guanigylhydrazone were synthesized and the biological activities test of representative target compounds showed that glycosyl aminoguanidine possessed preferable activities.
Keywords/Search Tags:Glycosyl isothiocyanate, formylpyrazole, glycosyl thiourea, glycosyl aminoguanidine, guanylhydrazon
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