Azide-enolate 1,3-dipolar cycloaddition in the synthesis of novel triazole-based miconazole analogues as promising antifungal agents

Seven miconazole analogs involving 1,4,5-tri and 1,5-disubstituted triazole moieties were synthesized by azide-enolate 1,3-dipolar cycloaddition. The antifungal activity of these compounds was evaluated in vitro against four filamentous fungi, including Aspergillus fumigatus, Trichosporon cutaneum,...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2016-04, Vol.112, p.60-65
Main Authors: González-Calderón, Davir, Mejía-Dionicio, María G., Morales-Reza, Marco A., Ramírez-Villalva, Alejandra, Morales-Rodríguez, Macario, Jauregui-Rodríguez, Bertha, Díaz-Torres, Eduardo, González-Romero, Carlos, Fuentes-Benítes, Aydeé
Format: Article
Language:English
Subjects:
1,2,3-Triazole derivatives
Antifungal activity
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Antifungal Agents - pharmacology
Aspergillus fumigatus - drug effects
Azide-enolate cycloaddition
Azides - chemical synthesis
Azides - chemistry
Candida - drug effects
Cycloaddition Reaction
Fungi - drug effects
Humans
Miconazole - chemical synthesis
Miconazole - chemistry
Miconazole - pharmacology
Miconazole analogs
Microbial Sensitivity Tests
Mycoses - drug therapy
Rhizopus - drug effects
Triazoles - chemical synthesis
Triazoles - chemistry
Triazoles - pharmacology
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Summary:Seven miconazole analogs involving 1,4,5-tri and 1,5-disubstituted triazole moieties were synthesized by azide-enolate 1,3-dipolar cycloaddition. The antifungal activity of these compounds was evaluated in vitro against four filamentous fungi, including Aspergillus fumigatus, Trichosporon cutaneum, Rhizopus oryzae, and Mucor hiemalis as well as three species of Candida spp. as yeast specimens. These pre-clinical studies suggest that compounds 4b, 4d and 7b can be considered as drug candidates for future complementary biological studies due to their good/excellent antifungal activities. [Display omitted] •Azide-enolate cycloaddition allowed for the synthesis of seven miconazole analogs.•Synthesis/evaluation of 1,4,5-tri and 1,5-disubstituted triazole derivatives.•Evaluation against four filamentous fungi and three species of yeast.•Compounds 4b, 4d and 7b have a good scope against Candida albicans and C. tropicalis.•A broader spectrum of 4d against filamentous fungi has been demonstrated.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2016.02.013