Synthesis and Antiviral Evaluation of (1,4-Disubstituted-1,2,3-Triazol)-(E)-2-Methyl-but-2-Enyl Nucleoside Phosphonate Prodrugs - Inserm - Institut national de la santé et de la recherche médicale Access content directly
Journal Articles Molecules Year : 2021

Synthesis and Antiviral Evaluation of (1,4-Disubstituted-1,2,3-Triazol)-(E)-2-Methyl-but-2-Enyl Nucleoside Phosphonate Prodrugs

Tuniyazi Abuduaini
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  • PersonId : 1115575
Vincent Roy
Tamara R Mcbrayer
  • Function : Author
  • PersonId : 1115578

Abstract

A series of hitherto unknown (1,4-disubstituted-1,2,3-triazol)-(E)-2-methyl-but-2-enyl nucleosides phosphonate prodrugs bearing 4-substituted-1,2,3-triazoles were prepared in a straight approach through an olefin acyclic cross metathesis as the key synthetic step. All novel compounds were evaluated for their antiviral activities against HBV, HIV and SARS-CoV-2. Among these molecules, only compound 15j, a hexadecyloxypropyl (HDP)/(isopropyloxycarbonyl-oxymethyl)-ester (POC) prodrug, showed activity against HBV in Huh7 cell cultures with 62% inhibition at 10 μM, without significant cytotoxicity (IC50 = 66.4 μM in HepG2 cells, IC50 = 43.1 μM in HepG2 cells) at 10 μM.
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inserm-03412066 , version 1 (02-11-2021)

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Tuniyazi Abuduaini, Vincent Roy, Julien Marlet, Catherine Gaudy-Graffin, Denys Brand, et al.. Synthesis and Antiviral Evaluation of (1,4-Disubstituted-1,2,3-Triazol)-(E)-2-Methyl-but-2-Enyl Nucleoside Phosphonate Prodrugs. Molecules, 2021, 26 (5), pp.1493. ⟨10.3390/molecules26051493⟩. ⟨inserm-03412066⟩
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