Document Type
Article
Publication Date
2014
Abstract
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.
Recommended Citation
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.
DOI:10.1139/cjc-2014-0356
Copyright
NRC Research Press
Comments
This is a pre-copy-editing, author-produced PDF of an article accepted for publication in Canadian Journal of Chemistry, 2014 following peer review. The definitive publisher-authenticated version is available online at DOI: 10.1139/cjc-2014-0356.