Metal-ion-binding analogs of ribonucleosides: Preparation and formation of ternary Pd2+ and Hg2+ complexes with natural pyrimidine nucleosides

Abstract

Four metal-ion-binding nucleosides, viz. 2,6-bis(1-methylhydrazinyl)-9-(β-D-ribofuranosyl)-9H-purine (2a) and its N-acetylated derivative, 2b, 2,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)-5-(β-D-ribofuranosyl)pyrimidine (3), and 2,4-bis(1-methylhydrazinyl)-5-(β-D-ribofuranosyl)pyrimidine (4) have been synthesized. The ability of these nucleosides and the previously prepared 2,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)-9-(β-D-ribofuranosyl)-9H-purine to form Pd2+- and Hg2+-mediated complexes with uridine has been studied by 1H-NMR spectroscopy. To obtain additional support for the interpretation of the NMR data, comparative measurements on the ternary-complex formation between pyridine-2,6-dicarboxamide (5), pyrimidine nucleosides, and K2PdCl4 were carried out. Copyright © 2013 Verlag Helvetica Chimica Acta AG, Zürich.