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Synthesis of N-tetra-O-acetyl-beta-D-glucopyranosyl-N'-(4',6'-diarylpyrimidin-2'-yl)thioureas

Synthesis of N-tetra-O-acetyl-beta-D-glucopyranosyl-N'-(4',6'-diarylpyrimidin-2'-yl)thioureas

Nguyen Dinh Thanh, Nguyen Thi Thanh Mai

Carbohydr Res. 2009 Nov 23;344(17):2399-405.

PMID: 19804880

Abstract:

Some 2-amino-4,6-diarylpyrimidines 2 have been prepared from substituted benzylideneacetophenones and guanidine hydrochloride in the presence of alkali by conventional heating in alcoholic medium and microwave heating in solvent-free conditions. N-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl)-N'-(4',6'-diarylpyrimidin-2'-yl)thioureas 4 have been synthesized by reaction of per-O-acetylated glucopyranosyl isothiocyanate 1 and substituted 2-amino-4,6-diarylpyrimidines 2. Two different methods have been used, namely, refluxing in anhydrous dioxane and solvent-free microwave-assisted coupling. The second procedure afforded higher yields in much shorter reaction times. The compounds 2 and 4 were tested for their antibacterial and antifungal activities in vitro against Staphylococcus epidermidis, Enterobacter aerogenes and Candida albicans by disc diffusion method.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP958300066	2,3,4,6-Tetra-O-pivaloyl-β-D-glucopyranosyl isothiocyanate		958300-06-6	Price

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