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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2025-05-01
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| author | 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 |
| author_facet | 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 |
| author_sort | Nathália L. B. Santos |
| collection | DOAJ |
| description | <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.. |
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| issn | 1424-8247 |
| language | English |
| publishDate | 2025-05-01 |
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| spelling | doaj-art-4070e06f29dc48c0b44fc02db0a8ee9f2025-06-25T14:17:31ZengMDPI AGPharmaceuticals1424-82472025-05-0118679710.3390/ph18060797Design, Synthesis, and In Vitro Evaluation of 4-(Arylchalcogenyl)methyl)-1H-1,2,3-triazol-1-yl-menadione: Exploring Their Potential Against <i>Tuberculosis</i>Nathália L. B. Santos0Luana S. Gomes1Ruan C. B. Ribeiro2Alcione S. de Carvalho3Maria Cristina S. Lourenço4Laís Machado Marins5Sandy Polycarpo Valle6Thiago H. Doring7Adriano D. Andricopulo8Aldo S. de Oliveira9Vitor F. Ferreira10Fernando de C. da Silva11Luana da Silva Magalhães Forezi12Vanessa Nascimento13Instituto de Química, Universidade Federal Fluminense, Campus do Valonguinho, Niterói 24020-141, RJ, BrazilInstituto de Química, Universidade Federal Fluminense, Campus do Valonguinho, Niterói 24020-141, RJ, BrazilInstituto de Química, Universidade Federal Fluminense, Campus do Valonguinho, Niterói 24020-141, RJ, BrazilInstituto de Química, Universidade Federal Fluminense, Campus do Valonguinho, Niterói 24020-141, RJ, BrazilLaboratório de Bacteriologia e Bioensaios, Campus Manguinhos—Fiocruz—Fiocruz, Rio de Janeiro 21040-361, RJ, BrazilInstituto de Química, Universidade Federal Fluminense, Campus do Valonguinho, Niterói 24020-141, RJ, BrazilInstituto de Química, Universidade Federal Fluminense, Campus do Valonguinho, Niterói 24020-141, RJ, BrazilDepartamento de Ciências Exatas e Educação (CEE), Centro Tecnológico, de Ciências Exatas e Educação (CTE), Universidade Federal de Santa Catarina (UFSC), Blumenau 89036-256, SC, BrazilLaboratório de Química Medicinal e Computacional (LQMC), Instituto de São Carlos de Física (IFSC), Universidade de São Paulo (USP), Av. João Dagnone, 1100, São Carlos 13563-120, SP, BrazilInstituto Gulbenkian Institute de Medicina Molecular (GIMM), Faculdade de Medicina, Universidade de Lisboa, 1649-028 Lisboa, PortugalDepartamento de Tecnologia Farmacêutica, Faculdade de Farmácia, Universidade Federal Fluminense, Niterói 24241-000, RJ, BrazilInstituto de Química, Universidade Federal Fluminense, Campus do Valonguinho, Niterói 24020-141, RJ, BrazilInstituto de Química, Universidade Federal Fluminense, Campus do Valonguinho, Niterói 24020-141, RJ, BrazilInstituto de Química, Universidade Federal Fluminense, Campus do Valonguinho, Niterói 24020-141, RJ, Brazil<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..https://www.mdpi.com/1424-8247/18/6/7971,4-naphthoquinonesseleniumsulfurCuAAC<i>Mycobacterium tuberculosis</i> H37Rv (ATCC 27294) |
| spellingShingle | 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 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> Pharmaceuticals 1,4-naphthoquinones selenium sulfur CuAAC <i>Mycobacterium tuberculosis</i> H37Rv (ATCC 27294) |
| title | 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> |
| title_full | 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> |
| title_fullStr | 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> |
| title_full_unstemmed | 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> |
| title_short | 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> |
| title_sort | 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 |
| topic | 1,4-naphthoquinones selenium sulfur CuAAC <i>Mycobacterium tuberculosis</i> H37Rv (ATCC 27294) |
| url | https://www.mdpi.com/1424-8247/18/6/797 |
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