A new class of nucleoside analogues were synthesized using cyclic dipeptides and modified 2′-deoxyfuranoribose sugars to introduce flexibility by peptides in place of common nucleoside bases and to determine their biological properties. The synthesis was carried out by coupling of a protected ribose sugar with synthesized dipeptides in the presence of hexamethyldisilazane and trimethylsilyltriflate. The final products were characterized by NMR and high-resolution MS-TOF spectroscopy. The compounds were evaluated for anti-HIV activities. 1-(4-Azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,6-diisopropylpiperazine-2,5-dione (compound 14) containing 3- and 6-isopropyl groups in the base and 3′-azide (EC50 = 1.96 μmol/L) was the most potent compound among all of the synthesized analogs.
Chhikara, B. S., Rao, M. S., Rao, V. K., Kumar, A., Buckheit, K. W., Buckheit Jr. R. W., Parang, K. Carbocyclodipeptides as modified nucleosides: Synthesis and anti-HIV activities. Can. J. Chem. (2014) 10.1139/cjc-2014-0356.
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