Design, Synthesis, and In Vitro Evaluation of 4-(Arylchalcogenyl)methyl)-1H-1,2,3-triazol-1-yl-menadione: Exploring Their Potential Against <i>Tuberculosis</i>

Design, Synthesis, and In Vitro Evaluation of 4-(Arylchalcogenyl)methyl)-1H-1,2,3-triazol-1-yl-menadione: Exploring Their Potential Against <i>Tuberculosis</i>

<b>Background/Objectives:</b> In this study, a novel series of 4-(arylchalcogenyl)methyl)-1H-1,2,3-Triazol-1-yl-menadione derivatives were synthesized to explore their potential as new antituberculosis (anti-TB) agents. Selenium-containing compounds are known for their significant antimy...

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Main Authors: Nathália L. B. Santos, Luana S. Gomes, Ruan C. B. Ribeiro, Alcione S. de Carvalho, Maria Cristina S. Lourenço, Laís Machado Marins, Sandy Polycarpo Valle, Thiago H. Doring, Adriano D. Andricopulo, Aldo S. de Oliveira, Vitor F. Ferreira, Fernando de C. da Silva, Luana da Silva Magalhães Forezi, Vanessa Nascimento
Format: Article
Language:English
Published: MDPI AG 2025-05-01
Series:Pharmaceuticals
Subjects:
1,4-naphthoquinones
selenium
sulfur
CuAAC
<i>Mycobacterium tuberculosis</i> H37Rv (ATCC 27294)
Online Access:https://www.mdpi.com/1424-8247/18/6/797
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Summary:<b>Background/Objectives:</b> In this study, a novel series of 4-(arylchalcogenyl)methyl)-1H-1,2,3-Triazol-1-yl-menadione derivatives were synthesized to explore their potential as new antituberculosis (anti-TB) agents. Selenium-containing compounds are known for their significant antimycobacterial activity, which motivated their inclusion in the design. <b>Methods:</b> The target compounds were synthesized via a copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, affording yields ranging from 34% to 93%. All compounds were evaluated in vitro for anti-TB activity against <i>Mycobacterium tuberculosis</i> H37Rv (ATCC 27294), as well as a drug-resistant strain (T113/09). <b>Results:</b> Several selenium-containing derivatives exhibited promising activity. Compounds <b>9b</b> and <b>9g</b> were equipotent to the first-line anti-TB drug, and one compound surpassed its activity. Notably, compounds <b>9a</b>, <b>9b</b>, <b>9g</b>, and <b>9h</b> also showed efficacy against the INH- and RIF-resistant <i>Mtb</i> strain T113/09. <b>Conclusions:</b> The efficacy of selenium-containing triazole-menadione hybrids against both sensitive and resistant <i>Mtb</i> strains highlight their potential as candidates for addressing antimicrobial resistance in TB treatment. Further investigations are required to understand their mechanisms of action and assess their in vivo therapeutic potential..
ISSN:1424-8247

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