Design, synthesis, docking studies and bioactivity evaluation of 1,2,3-triazole eugenol derivatives
<b>Aim:</b> The design, synthesis, docking studies and evaluation of the <i>in vitro</i> antifungal and cytotoxic properties of eugenol (EUG) containing 1,2,3-triazole derivatives are reported. Most of the derivatives have not been reported.<b>Materials & methods:</b> The EUG derivatives were synthesized, molecular docked and tested for their antifungal activity.<b>Results:</b> The compounds showed potent antifungal activity against <i>Trichophyton rubrum</i>, associated with dermatophytosis. Compounds <b>2a</b> and <b>2i</b> exhibited promising results, with <b>2a</b> being four-times more potent than EUG. The binding mode prediction was similar to itraconazole in the lanosterol-14-α-demethylase wild-type and G73E mutant binding sites. Additionally, the pharmacokinetic profile prediction suggests good gastrointestinal absorption and potential oral administration.<b>Conclusion:</b> Compound <b>2a</b> is a promising antifungal agent against dermatophytosis caused by <i>T. rubrum</i>.
Authors
- Leandra Martins Meireles (ORCID: https://orcid.org/0000-0003-0289-3669)
- Cláudia Jorge do Nascimento (ORCID: https://orcid.org/0000-0001-8896-8654)
- Adílson Vidal Costa (ORCID: https://orcid.org/0000-0002-7968-8586)
- Luiz C. A. Barbosa (ORCID: https://orcid.org/0000-0002-5395-9608)
- Pedro Alves Bezerra Morais (ORCID: https://orcid.org/0000-0001-5501-7350)
- Fernando Fontes Barcelos (ORCID: https://orcid.org/0000-0001-5914-9924)
- Róbson Ricardo Teixeira (ORCID: https://orcid.org/0000-0003-3181-1108)
- Luíza Carvalheira Moreira (ORCID: https://orcid.org/0000-0002-9654-8622)
- Ângela Maria Almeida Lima (ORCID: https://orcid.org/0000-0002-8455-6289)
- J. Junker (ORCID: https://orcid.org/0000-0003-4002-4405)
- Thiago Antônio de Sousa Cutrim (ORCID: https://orcid.org/0000-0002-8986-8855)
- Márcio Fronza (ORCID: https://orcid.org/0000-0002-7316-8598)
- Vagner Tebaldi de Queiroz (ORCID: https://orcid.org/0000-0002-8170-125X)
- Rodrigo Scherer (ORCID: https://orcid.org/0000-0001-7656-0248)
- Poliana Aparecida Rodrigues Gazolla (ORCID: https://orcid.org/0000-0002-0613-9092)
Institutions
- Universidade Federal de Minas Gerais (BR)
- Universidade Federal de Viçosa (BR)
- Universidade Vila Velha (BR)
- Universidade Federal do Espírito Santo (BR)
- Fundação Oswaldo Cruz (BR)
- Universidade Federal do Estado do Rio de Janeiro (BR)
Publication Details
- Journal
- Future Medicinal Chemistry
- Published
- 2024-08-19
- DOI
- https://doi.org/10.1080/17568919.2024.2385292
- Citations
- 2
- Primary Topic
- Click Chemistry and Applications
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
- Conselho Nacional de Desenvolvimento Científico e Tecnológico
- Fundação de Amparo à Pesquisa do Estado de Minas Gerais
- Fundação de Amparo à Pesquisa e Inovação do Espírito Santo