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An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids.

ABSTRACT: 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-5-chloropyrimidin-2-ylphosphonic acid (7a) was found to exhibit a weak to moderate anti-influenza activity (28-50 ?M) and may represent a novel hit for further SAR studies and antiviral improvement.

SUBMITTER: Jansa P

PROVIDER: S-EPMC7125588 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

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An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids.

Jansa Petr P Hradil Ondřej O Baszczyňski Ondřej O Dračínský Martin M Klepetářová Blanka B Holý Antonín A Balzarini Jan J Janeba Zlatko Z

Tetrahedron 20111119 3

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-5-chloropyrimidin-2-ylphosphonic acid (<b>7a</b>) was found to exhibit a weak to moderate anti-influen ...[more]

PMID: 32287424

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