Development of Triazoles and Triazolium Salts Based on AZT and Their Anti-Viral Activity against HIV-1

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...

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Autores principales:	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
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	click chemistry triazoles triazolium salts anti-viral HIV-1 AZT Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/0091e9d5698e4f5bb5caca695adc3782
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spelling	oai:doaj.org-article:0091e9d5698e4f5bb5caca695adc37822021-11-11T18:39:40ZDevelopment of Triazoles and Triazolium Salts Based on AZT and Their Anti-Viral Activity against HIV-110.3390/molecules262167201420-3049https://doaj.org/article/0091e9d5698e4f5bb5caca695adc37822021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6720https://doaj.org/toc/1420-3049We 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.Daniel Machado de AlencarJuliana GonçalvesAndreia VieiraSofia A. CerqueiraCruz SebastiãoMaria Inês P. S. LeitãoGiulia FrancescatoPaola AntenoriHelena SoaresAna PetronilhoMDPI AGarticleclick chemistrytriazolestriazolium saltsanti-viralHIV-1AZTOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6720, p 6720 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	click chemistry triazoles triazolium salts anti-viral HIV-1 AZT Organic chemistry QD241-441
spellingShingle	click chemistry triazoles triazolium salts anti-viral HIV-1 AZT Organic chemistry QD241-441 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 Development of Triazoles and Triazolium Salts Based on AZT and Their Anti-Viral Activity against HIV-1
description	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.
format	article
author	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
author_facet	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
author_sort	Daniel Machado de Alencar
title	Development of Triazoles and Triazolium Salts Based on AZT and Their Anti-Viral Activity against HIV-1
title_short	Development of Triazoles and Triazolium Salts Based on AZT and Their Anti-Viral Activity against HIV-1
title_full	Development of Triazoles and Triazolium Salts Based on AZT and Their Anti-Viral Activity against HIV-1
title_fullStr	Development of Triazoles and Triazolium Salts Based on AZT and Their Anti-Viral Activity against HIV-1
title_full_unstemmed	Development of Triazoles and Triazolium Salts Based on AZT and Their Anti-Viral Activity against HIV-1
title_sort	development of triazoles and triazolium salts based on azt and their anti-viral activity against hiv-1
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/0091e9d5698e4f5bb5caca695adc3782
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Development of Triazoles and Triazolium Salts Based on AZT and Their Anti-Viral Activity against HIV-1

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