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1-Benzyl derivatives of 5-(arylamino)uracils as anti-HIV-1 and anti-EBV agents
- Source :
- Bioorganic & Medicinal Chemistry. 18:8310-8314
- Publication Year :
- 2010
- Publisher :
- Elsevier BV, 2010.
-
Abstract
- 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.
- Subjects :
- Herpesvirus 4, Human
Pyrimidine
Anti-HIV Agents
Stereochemistry
Clinical Biochemistry
Pharmaceutical Science
Antiviral Agents
Biochemistry
Chemical synthesis
Cell Line
chemistry.chemical_compound
Pyrimidine analogue
Benzylamine
Drug Discovery
Humans
heterocyclic compounds
Uracil
Molecular Biology
Amination
Chemistry
Organic Chemistry
Biological activity
In vitro
HIV-1
Molecular Medicine
Subjects
Details
- ISSN :
- 09680896
- Volume :
- 18
- Database :
- OpenAIRE
- Journal :
- Bioorganic & Medicinal Chemistry
- Accession number :
- edsair.doi.dedup.....f3b5a6ff165daecf382b9b55e13987fc