Development of triazoles and triazolium salts based on azt and their anti-viral activity against hiv-1

Daniel Machado de Alencar, Juliana Gonçalves, Andreia Vieira, Sofia A. Cerqueira, Cruz Sebastião, Maria Inês P.S. Leitão, Giulia Francescato, Paola Antenori, Helena Soares, Ana Petronilho

Research output: Contribution to journalArticlepeer-review

Abstract

We report herein a set of 3-azido-3-deoxythymidine (AZT) derivatives based on triazoles and triazolium salts for HIV-1 infection. The compounds were synthesized via click chemistry with Cu(I) and Ru(II) catalysts. Triazolium salts were synthesized by reaction with methyl iodide or methyl triflate in good yields. The antiviral activity of the compounds was tested using two methodologies: In method one the activity was measured on infected cells; in method two a pre-exposure prophylaxis experimental model was employed. For method one the activity of the compounds was moderate, and in general the triazolium salts showed a decreased activity in relation to their triazole precursors. With method two the antiviral activity was higher. All compounds were able to decrease the infection, with two compounds able to clear almost all the infection, while a lower antiviral activity was noted for the triazolium salts. These results suggest that these drugs could play an important role in the development of pre-exposure prophylaxis therapies.

Original languageEnglish
Article number6720
JournalMolecules
Volume26
Issue number21
DOIs
Publication statusPublished - 1 Nov 2021

Keywords

  • Anti-viral
  • AZT
  • Click chemistry
  • HIV-1
  • Triazoles
  • Triazolium salts

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