An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids
Jansa, Petr × Hradil, Ondrej Baszczynski, Ondrej Dracinsky, Martin Klepetarova, Blanka Holy, Antonin Balzarini, Jan Janeba, Zlatko #
Tetrahedron vol:68 issue:3 pages:865-871
Polysubstituted pyrimidinylphosphonic and 1,3,5-triazinylphosphonic acids with potential biological properties were prepared in high yields by the microwave-assisted Michaelis Arbuzov reaction of trialkyl phosphite with the corresponding halopyrimidines and halo-1,3,5-triazines, respectively, followed by the standard deprotection of the phosphonate group using TMSBr in acetonitrile. 4,6-Diamino-5chloropyrimidin-2-ylphosphonic acid (7a) was found to exhibit a weak to moderate anti-influenza activity (28-50 uM) and may represent a novel hit for further SAR studies and antiviral improvement. (C) 2011 Elsevier Ltd. All rights reserved.