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Bioorg Med Chem. 2010 Dec 1;18(23):8310-4. doi: 10.1016/j.bmc.2010.09.070. Epub 2010 Oct 7.

1-Benzyl derivatives of 5-(arylamino)uracils as anti-HIV-1 and anti-EBV agents.

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Department of Pharmaceutical & Toxicological Chemistry, Volgograd State Medical University, Russia.


Pyrimidine analogs have long found use over a broad chemotherapeutic spectrum. In an effort to further explore the antiviral potential of several uracil derivatives previously synthesized in our laboratories, a series of benzylated pyrimidines were designed and synthesized. Introduction of the benzyl residue onto the 5-phenylaminouracil scaffold was carried out using 2,4-bis(trimethylsilyloxy)pyrimidine with the corresponding benzyl bromides. Similarly, 1-benzyl-5-(benzylamino)- and 1-benzyl-5-(phenethylamino)uracils were obtained via amination of 1-benzyl-5-bromouracils with benzylamine or phenylethylamine. The results of the broad screen antiviral studies revealed that compounds 5 and 11 exhibit promising inhibitory activity against HIV-1 in CEM-SS culture. A 50% protective effect was observed at concentrations of 11.9 and 9.5 μМ, respectively. Moreover, compounds 8 and 3 exhibited good inhibitory effects against EBV in АKАТА cell culture with EC₅₀ values of 2.3 and 12 μM, respectively. The synthesis and biological studies are detailed herein.

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