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Full-Text Articles in Carbohydrates
Carbocyclodipeptides As Modified Nucleosides: Synthesis And Anti- Hiv Activities, Bhupender S. Chhikara, M. Sudershan Rao, V. Kameshwara Rao, Anil Kumar, Karen W. Buckheit, Robert W. Buckheit Jr., Keykavous Parang
Carbocyclodipeptides As Modified Nucleosides: Synthesis And Anti- Hiv Activities, Bhupender S. Chhikara, M. Sudershan Rao, V. Kameshwara Rao, Anil Kumar, Karen W. Buckheit, Robert W. Buckheit Jr., Keykavous Parang
Pharmacy Faculty Articles and Research
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.