Synthesis and Evaluation of Antimicrobial Activity of Some Pyrimidine Glycosides

Autor:	Ibrahim M. Abdou, Hassan A. El-Sayed, Abd El‐Fattah Z. Haikal, Ahmed H. Moustafa, E. S. H. El‐Ashry
Rok vydání:	2008
Předmět:	chemistry.chemical_classification Magnetic Resonance Spectroscopy Bacteria Molecular Structure Pyrimidine Glycoside General Medicine Antimicrobial Biochemistry chemistry.chemical_compound Pyrimidines Anti-Infective Agents chemistry Bromide Ribose Genetics Molecular Medicine Organic chemistry Glycosides Methanol Microwaves
Zdroj:	Nucleosides, Nucleotides and Nucleic Acids. 27:1061-1071
ISSN:	1532-2335 1525-7770
Popis:	Reaction of ethyl 4-thioxo-3,4-dihydropyrimidine-5-carboxylate derivatives 1a,b and ethyl 4-oxo-3,4-dihydropyrimidine-5-carboxylate 1c with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide in KOH or TEA afforded ethyl 2-aryl-4-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosylthio or/ oxy)-6-methylpyrimidine-5-carboxylate 6a-c. The glucosides 6a and 6b were obtained by the reaction of 1a and 1b with peracetylated glucose3 under MW irradiation. Mercuration of 1a followed by reaction with acetobromoglucose gave the same product 6a. The reaction of 1a-c with peracetylated ribose 4 under MW irradiation gave ethyl 2-aryl-4-(2',3',5'-tri-O-acetyl-beta-D-ribofuranosylthio)-6-methylpyrimidine-5-carboxylate 8a-c. The deprotection of 6a-c and 8a-c in the presence of methanol and TEA/H(2)O afforded the deprotected products 7a-c and 9a-c. The structure were confirmed by using (1)H and (13)CNMR spectra. Selected members of these compounds were screened for antimicrobial activity.
Databáze:	OpenAIRE
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