Synthesis and antimicrobial activity of some S-beta-D-glucosides of 4-mercaptopyrimidine.
5-Acetyl-2-aryl-6-methyl-4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylmercapto)pyramidines 3a-c were obtained by the reaction of 5-acetyl-2-aryl-6-methyl-pyrimidine thiol 1a-c with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide (2) in aq. KOH/acetone. The reaction of 1a-c with peracetylated galactose 5 and peracetylated ribose 8 under MW irradiation gave 5-acetyl-2-aryl-6-methyl-4-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosylmercapto)pyrimidine 6a-c and 5-acetyl-2-aryl-6-methyl-4-(2,3,5-tri-O-acetyl-beta-D-ribofuranosylmercapto)pyrimidines 9a-c. The deprotection of 3a-c, 6a-c, and 9a-c in the presence of methanol and TEA/H(2)O yielded the deprotected products 4a-c, 7a-c, and 10a-c. The structures of the compounds were confirmed by using IR, (1)H, (13)C spectra and microanalysis. Selected members of these compounds were screened for antimicrobial activity.
Moustafa
A H
AH
Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt. ah hu mostafa@yahoo.com
Morsy
H A
HA
Assy
M G
MG
Haikal
A Z
AZ
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011741:Pyrimidine Nucleosides / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000890:Anti-Infective Agents; D005960:Glucosides; D011741:Pyrimidine Nucleosides; D013438:Sulfhydryl Compounds