Synthesis and evaluation of antimicrobial activity of some pyrimidine glycosides

Nucleosides, Nucleotides & Nucleic Acids
Hassan A El-SayedE S H El-Ashry

Abstract

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.

References

May 7, 2002·Nucleosides, Nucleotides & Nucleic Acids·Mariola AndrzejewskaZygmunt Kazimierczuk
Oct 10, 2003·Nucleosides, Nucleotides & Nucleic Acids·Abdel Kader MansourNasser S A M Khalil
Oct 24, 2003·Carbohydrate Research·Abdellfattah Z HaikalJoseph Banoub
Dec 19, 2003·Nucleosides, Nucleotides & Nucleic Acids·Adel A H Abdel-RahmanEl Sayed H El Ashry
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Dec 13, 2006·Nucleosides, Nucleotides & Nucleic Acids·Mariola Koszytkowska-StawińskaErik De Clercq

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Citations

Mar 2, 2011·Nucleosides, Nucleotides & Nucleic Acids·Shaikha S Al-NeyadiIbrahim M Abdou
Jul 22, 2011·Nucleosides, Nucleotides & Nucleic Acids·Ahmed H MoustafaEl Sayed H El Ashry
Nov 14, 2012·Nucleosides, Nucleotides & Nucleic Acids·Abdalla E A HassanAbdelfattah Z Haikal
Oct 2, 2013·Nucleosides, Nucleotides & Nucleic Acids·Nora M RatebIbrahim M Abdou
Feb 26, 2010·Nucleosides, Nucleotides & Nucleic Acids·A H MoustafaA Z Haikal
May 3, 2011·European Journal of Medicinal Chemistry·Hassan A El-SayedEl Sayed H El Ashry
Jul 6, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hosam A Saad, Ahmed H Moustafa
Feb 8, 2019·Nucleosides, Nucleotides & Nucleic Acids·Galal H ElgemeieReham A Mohamed

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Methods Mentioned

BETA
NMR

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