1,6-Bis[(benzyloxy)methyl]uracil derivatives—Novel antivirals with activity against HIV-1 and influenza H1N1 virus

Bioorganic & Medicinal Chemistry
2016.0

Abstract

A series of 1,6-bis[(benzyloxy)methyl]uracil derivatives combining structural features of both diphenyl ether and pyridone types of NNRTIs were synthesized. Target compounds were found to inhibit HIV-1 reverse transcriptase at micro- and submicromolar levels of concentrations and exhibited anti-HIV-1 activity in MT-4 cell culture, demonstrating resistance profile similar to first generation NNRTIs. The synthesized compounds also showed profound activity against influenza virus (H1N1) in MDCK cell culture without detectable cytotoxicity. The lead compound of this assay appeared to exceed rimantadine, amantadine, ribavirin and oseltamivir carboxylate in activity. The mechanism of action of 1,6-bis[(benzyloxy)methyl]uracils against influenza virus is currently under investigation.

Knowledge Graph

Similar Paper

1,6-Bis[(benzyloxy)methyl]uracil derivatives—Novel antivirals with activity against HIV-1 and influenza H1N1 virus
Bioorganic & Medicinal Chemistry 2016.0
1-[2-(2-Benzoyl- and 2-benzylphenoxy)ethyl]uracils as potent anti-HIV-1 agents
Bioorganic & Medicinal Chemistry 2011.0
N1,N3-disubstituted uracils as nonnucleoside inhibitors of HIV-1 reverse transcriptase
Bioorganic & Medicinal Chemistry 2013.0
Synthesis and evaluation of novel 3-(3,5-dimethylbenzyl)uracil analogs as potential anti-HIV-1 agents
Bioorganic & Medicinal Chemistry 2013.0
1-Benzyl derivatives of 5-(arylamino)uracils as anti-HIV-1 and anti-EBV agents
Bioorganic & Medicinal Chemistry 2010.0
Synthesis and antiviral activity of substituted bisaryl amide compounds as novel influenza virus inhibitors
European Journal of Medicinal Chemistry 2012.0
Synthesis and Antiviral Activity Evaluation of Some New Aminoadamantane Derivatives. 2
Journal of Medicinal Chemistry 1996.0
Synthesis and Antiviral Activity of 6-Benzyl Analogs of 1-[(2-Hydroxyethoxy)methyl]-5-(phenylthio)thymine (HEPT) as Potent and Selective Anti-HIV-1 Agents
Journal of Medicinal Chemistry 1995.0
Scaffold hopping: Exploration of acetanilide-containing uracil analogues as potential NNRTIs
Bioorganic & Medicinal Chemistry 2015.0
Design, Synthesis, and Biological Evaluation of 1-[(2-Benzyloxyl/alkoxyl)methyl]-5-halo-6-aryluracils as Potent HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors with an Improved Drug Resistance Profile
Journal of Medicinal Chemistry 2012.0