Abstract
Pyrimidines, such as 6-amino-2-thio and 2-methylthiouracils and fused pyrimidines, such as thienopyrimidines reacted with 1-O-acetyl-2,3,5-tri-O- benzoyl-β-D-ribofuranose to get new derivatives of the corresponding nucleosides. The obtained protected nucleosides were deprotected by methanolic sodium methoxide to get the corresponding free uracil and thienopyrimidine nucleosides. The new nucleosides formed were tested for biological activity against some of microorganism (some fungi and bacteria species). Some of the tested products showed moderate activity and the results were reported.
Highlights
Pyrimidines and their fused derivatives form the heterocyclic core of nucleic acid bases
Each of the silylated compounds 2a or 2b was stirred with the protected ribose 3 in dry 1,2-dichloroethane and trimethylsilane triflate; CF3SO2OSiMe3 as a catalyst at room temperature for 24 hours
This method yielded the benzoylated N-nucleosides, 6-amino-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-thio and 2-methylthiouracil (4a) or (4b), respectively, which hitherto have not been reported in literature yet
Summary
Pyrimidines and their fused derivatives form the heterocyclic core of nucleic acid bases. These ring systems are incorporated into drugs used for AIDS, cancer and anti-viral treatment. Up-to-date synthetic strategies of the acyclic and cyclic pyridinethione nucleosides including their aza- and deaza-analogs have been exploited and highlighted throughout a review in 2019 [10]. For these biological and medicinal purposes and others, it is important to develop the field of the synthesis of nucleosides. The biological activities of the new prepared nucleosides were tested using some of microorganisms
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