We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Carbocyclodipeptides as modified nucleosides: synthesis and anti-HIV activities.
- Authors
Chhikara, Bhupender S.; Rao, M. Sudershan; Rao, V. Kameshwara; Kumar, Anil; Buckheit, Karen W.; Buckheit Jr., Robert W.; Parang, Keykavous
- 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.
- Subjects
NUCLEOSIDES; PEPTIDES; CHEMICAL synthesis; RIBOSE; TIME-of-flight mass spectrometry
- Publication
Canadian Journal of Chemistry, 2014, Vol 92, Issue 12, p1145
- ISSN
0008-4042
- Publication type
Article
- DOI
10.1139/cjc-2014-0356