Synthesis of N-tetra-O-acetyl-beta-D-glucopyranosyl-N'-(4',6'-diarylpyrimidin-2'-yl)thioureas.
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.
Thanh
Nguyen Dinh
ND
Faculty of Chemistry, College of Science, Hanoi National University, 19 Le Thanh Tong, Hanoi 10000, Viet Nam. nguyendinhthanh@hus.edu.vn
Mai
Nguyen Thi Thanh
NT
D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D021902:Enterobacter aerogenes / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D011743:Pyrimidines / Q000138:chemical synthesis*; D013212:Staphylococcus epidermidis / Q000187:drug effects; D013890:Thiourea / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D011743:Pyrimidines; D013890:Thiourea; D000117:Acetylglucosamine