1-(Ethoxymethyl)-6-(Phenylselenenyl)Pyrimidines with Activity against Human Immunodeficiency Virus Types 1 and 2

doi:10.1177/095632029200300502

Paper

1-(Ethoxymethyl)-6-(Phenylselenenyl)Pyrimidines with Activity against Human Immunodeficiency Virus Types 1 and 2

Published Oct 1, 1992 · N. Goudgaon, A. Mcmillan, R. Schinazi

Antiviral Chemistry and Chemotherapy

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25

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Abstract

The reaction of chloromethyl ethyl ether with bis(trimethylsilyl)uracil derivatives yield 1-(ethoxymethyl)pyrimidines 1a–d in good yield. Lithiation of 1a–d with lithium diisopropylamide at −78°C, followed by reaction with diphenyl diselenide as an electrophile, gave 1-(ethoxymethyl)-6-(phenylselenenyl)ura-cils 2a–d in 70–80% yield. The 6-phenylselenenyl acyclic pyrimidines 2b and 2d exhibited selective in vitro activity against HIV-1 and HIV-2 in primary human lymphocytes. The most potent compound was 1-(ethoxymethyl)-6-(phenylselenenyl)-5-ethyluracil 2d with a median effective concentration of 17 nM in primary human lymphocytes and no discernable cytotoxicity in these cells or rapidly dividing CEM and Vero cells. Well characterized AZT-resistant virus was modestly (3 to 12-fold increase) cross-resistant to compounds 2b and 2d.

In Vitro Study

Study Snapshot

1-(ethoxymethyl)-6-(phenylselenenyl)pyrimidines show selective in vitro activity against HIV-1 and HIV-2 in primary human lymphocytes, with minimal cytotoxicity and modest cross-resistance to AZT-resistant viruses.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

1-(Ethoxymethyl)-6-(Phenylselenenyl)Pyrimidines with Activity against Human Immunodeficiency Virus Types 1 and 2

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References

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6-phenylselenenyl acyclonucleosides show potential as antiviral agents against HIV-1 and HIV-2 in primary human lymphocytes, with a different mechanism of action than related HEPT compounds.

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Citations

Synthesis and Antiviral Efficacy of Pyrimidine Analogs Targeting Viral Pathways

Pyrimidine analogs show potential in treating viral infections with their target-specific antiviral potential, offering a potential alternative to existing antiviral drugs.

A comprehensive review on pyrimidine analogs-versatile scaffold with medicinal and biological potential

Pyrimidine analogs are a versatile scaffold with potential medicinal and biological activities, making them an attractive scaffold for the discovery of new drugs with diverse properties.

Combined structure- and ligand-based virtual screening aiding discovery of selenoglycolicamides as potential multitarget agents against Leishmania species

Selenoglycolicamides 6, 7, 10, 12 and 13 show potential as new drug candidates against Leishmania species, showing activity against four strategic enzymes.

Novel HIV-1 non-nucleoside reverse transcriptase inhibitors: A combinatorial approach

A combinatorial approach using pyrimidine derivatives can create highly potent novel HIV-1 non-nucleoside reverse transcriptase inhibitors, potentially improving efficacy in combating HIV infection.

Synthesis of new organochalcogen (Se or Te) based multifunctional pyrimidine derivatives: X-ray structure determination of 2,4-bis(arylchalcogenyl)pyrimidine and 2-chloro-4,6-bis(arylchalcogenyl)pyrimidine compounds

This study synthesized a new class of organochalcogen (Se or Te) based multifunctional pyrimidine derivatives, revealing their crystal structures and spectroscopic characterizations.