The Synthesis Of Galactosyl And Bisglycosyl Guanidines

Guanidines play an important role in many biological activity, some of them have shown strong antimicrobial, defervescence, antitumor activity. Some guanidines have been found to show antiinfluenza and anti-HIV activity. Most of the compounds with single or mutiple gunidine functional groups isolated from natural products have a wide range of antiviral and antitumor biological activities or pharmacological uses such as therapy for the hypertension and treatment of diabetes. Glyguanidines as the derivatives of carbohydrates and guanidines have attracted considerable attention of the pharmaceutical industry for the remarkable ability to prevent the proliferation of HIV. A number of thiazole compounds have been reported to exhibit antibacterical and bactericidal activity. Herein we designed and synthesized guanidine moieties containing galactosyl fragments as well as thiazole ring from reaction of alkyl or aryl amine with thiourea which was synthesized by reactions of galactosyl isothiocyanate with 2-amino-4-arylthiazoles, and HgCl2 was used as catalyzer. And some novel bisglycosyl (glucosyl, galactosyl and lactosyl) guanidines were synthesized from reaction of 2-amino-4/6-substituted-benzothiazole with bisglycosyl thioureas which were synthesized by glycosyl isothiocyanate.The structure of all the synthesized compounds was confirmed by IR, NMR and MS spectral data and analytical analysis.The major accomplishments of this treatise:1. Galactosylthiourea were synthesized by the reaction of 2-amino-4-arylthiazoles with galactosyl isothocyanate, subsequent a series of novel galactosylguanidines were prepared by guanylation of the resulting thiourea with amine in presence of mercuric chloride.2. N′, N″-bis-(O-protected-glycosyl)thioureas were synthesized by dimerization of glycosyl isothiocyanates. And desired N-(4/6-substituted-benzothiazole-2-yl)-N′,N″-bis-(O-protected- glycosyl) guanidines were synthesized by the reaction of the thioureas with 2-amino-4/6-substituted-benzothiazole in the presence of Hg2+ salts (HgCl2 or HgO).The major innovations of this treatise:1. A novel class of trisubstituted galactosyl guanidines was obtained under mild conditions and with high yields when utilizing HgCl2 as desulfurizing reagent. All compounds haven't been reported in the literatures. And the 1H NMR and 13C NMR chemical shifts of the compounds were assigned using both 1D and 2D techniques, including 1H NMR, 13C NMR, 1H-1H COSY, g HMQC, g HMBC and NOSEY. 2. N-(4/6-substituted-benzothiazole-2-yl)-N′,N″-bis-(O-protected-glycosyl)guanidines were synthesized by utilizing HgCl2 or HgO as desulfurizing reagent, meanwhile, the different mechanisms of desulfurization were discussed after careful study.