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Synthesis and antimicrobial activity of some S-beta-D-glucosides of 4-mercaptopyrimidine. 2009

A H Moustafa, and H A Morsy, and M G Assy, and A Z Haikal
Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt. ah hu mostafa@yahoo.com

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.

UI MeSH Term Description Entries
D011741 Pyrimidine Nucleosides Pyrimidines with a RIBOSE attached that can be phosphorylated to PYRIMIDINE NUCLEOTIDES. Nucleosides, Pyrimidine
D005960 Glucosides A GLYCOSIDE that is derived from GLUCOSE. Glucoside
D000890 Anti-Infective Agents Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. Anti-Infective Agent,Anti-Microbial Agent,Antimicrobial Agent,Microbicide,Microbicides,Anti-Microbial Agents,Antiinfective Agents,Antimicrobial Agents,Agent, Anti-Infective,Agent, Anti-Microbial,Agent, Antimicrobial,Agents, Anti-Infective,Agents, Anti-Microbial,Agents, Antiinfective,Agents, Antimicrobial,Anti Infective Agent,Anti Infective Agents,Anti Microbial Agent,Anti Microbial Agents
D013438 Sulfhydryl Compounds Compounds containing the -SH radical. Mercaptan,Mercapto Compounds,Sulfhydryl Compound,Thiol,Thiols,Mercaptans,Compound, Sulfhydryl,Compounds, Mercapto,Compounds, Sulfhydryl
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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