Synthesis And Biological Activity Of Glucosylguanidines And Glycosylamino-oxadiazoles,-thiadiazoles

Substituted guanidines are found in many compounds of medicinal interest. For example, they have shown a strong antihypertensive effect; some have been reported to show antitubercular, antimalarial, and antimicrobial activity. Recently, Guanidine-containing sugar have attracted the attention of pharmaceutical industry, Guanidine-containing sugar have exhibitted anti-influenza and anti-HIV. 1,3,4-oxadiazoles or 1,3,4-thiadiazoles are broadly used as herbicides, growth hormone, bactericides, effective insecticides, fungicides, and antiphlogistic. This two kinds of compounds have wide applicative, in addition, use of sugar cores should lead to potentially biodegradable, non-toxic and chiral dendrimers. Therefore, we expect to realize reinforcement of Physiological activities by means of combining the glycosyl with guanidines and 1,3,4-oxadiazoles or 1,3,4-thiadiazoles. Due to this wide range of biological activities, we considered it interesting to synthesize and evaluate the biological activity of some N-alky/aryl-N′-(4-arylthiazol-2-yl)-N′′-glucosyl-guanidines and 2-aryloxymethyl-5-glycosylamino-1,3,4-oxadiazoles, 1,3,4-thiadiazoles. All the compounds synthesized were conformed by data of 1H NMR, IR, MS (ESI), and elemental analysis. Pharmacological tests showed that some of the new compounds possessed pronounced anti-HIV activities. The mainly works in this paper: 1. 2-Amino-4-arylthiazoles were refluxed with glucosylisothocyantes to prepare the glucosylthiourea, Sudsequent desulfurization of the resulting thiourea with mercuric chloride in presence of amine gave glucosylguanidines, deacetylation using MeONa/MeOH. 2. Synthesis the N-glycosyl-N′-aryloxyacetylthiosemicarbazides, then cyclization of the thiourea to generate 2-aryloxymethyl-5-glycosylamino-1,3,4-oxadiazoles in presence of...