Synthesis, characterization and biological evaluation of C5'-N-cyclopropylcarboxamido-C6-amino-C2-alkynylated purine nucleoside analogues.

In an effort to develop potent antibacterial and anticancer agents, a series of C5'-N-cyclopropylcarboxamido-C6-amino-C2-alkynylated purine nucleoside analogues 11a-g were synthesized through a Sonogashira cross-coupling reaction. The nine-step synthesis is easy to perform, and employs commercially available reagents. 2-Iodo-5'-N-cyclopropylcarboxamidoadenosine (9) was used as the starting intermediate for the synthesis of title derivatives 11a-g. Synthetic intermediates (2-9) and final products (11a-g) were appropriately characterized by IR, H NMR, C NMR and mass spectroscopy. The synthesized purine nucleoside analogues (11a-g) were evaluated for their in vitro antibacterial activity against two gram-positive and two gram-negative bacteria. They were then tested for cytotoxicity against MDA-MB-231 and Caco-2 cancer cell lines to determine their anti-cancer activity. Among the tested compounds, compounds 11c and 11g showed most potent antibacterial activity against S.aureus and P.aeruginosa bacterial strains. Compounds 11b and 11e displayed considerable IC of 7.9 and 6.8 µg/mL, respectively, vs MDA-MB-231 cell lines of 7.5 and 8.3 µg/mL, respectively, against the Caco-2 cell lines.