Synthesis of Novel Benzylic 1,2,3-triazole-4-carboxamides and their in vitro Activity Against Clinically Common Fungal Species

Authors

  • Davir González-Calderón Universidad Autónoma del Estado de México
  • Ricardo García-Monroy Universidad Autónoma del Estado de México
  • Alejandra Ramírez-Villalva Universidad Autónoma del Estado de México
  • Salvador Mastachi-Loza Universidad Autónoma del Estado de México
  • José G. Aguirre-de Paz Universidad Autónoma del Estado de México
  • Aydee Fuentes-Benítes Universidad Autónoma del Estado de México
  • Carlos González-Romero Universidad Autónoma del Estado de México

DOI:

https://doi.org/10.29356/jmcs.v65i2.1457

Keywords:

1,2,3-Triazoles, antifungal activity, 1,3-dipolar cycloaddition, Rhizopus oryzae

Abstract

Abstract. A library of novel benzylic 1,2,3-triazole-4-carboxamides (3a-m) were obtained with acceptable yields via a one-pot procedure. The series of compounds was screened for fungicidal activity and evaluated in vitro against four filamentous fungi and four Candida species. The former consisted of Aspergillus fumigatus, Trichosporon cutaneum, Rhizopus oryzae and Mucor hiemalis, and the latter C. krusei, C. albicans, C. utilis and C. glabrata. According to the in vitro assays, 3d and 3e were the most efficient fungicidal agents (of all the test compounds) against R. oryzae, even better than the reference drug (itraconazole). Thus, 3d and 3e represent important scaffolds that can be modified to increase antifungal activity. Additionally, they are candidates for complementary studies on the inhibition of clinical infections produced by Rhizopus spp. strains.

 

Resumen. Se obtuvo una librería de nuevos bencil 1,2,3-triazoles-4-carboxamidas (3a-m) con rendimientos aceptables mediante un procedimiento one-pot. La serie de compuestos se seleccionó para determinar la actividad fungicida llevando a cabo una evaluación in vitro contra cuatro hongos filamentosos y cuatro especies de Candida. Los primeros consistieron en Aspergillus fumigatus, Trichosporon cutaneum, Rhizopus oryzae y Mucor hiemalis, mientras que para las segundas especies, esta fueron C. krusei, C. albicans, C. utilis y C. glabrata. Según los ensayos in vitro, 3d y 3e fueron los agentes fungicidas más eficaces (de todos los compuestos de prueba) contra R. oryzae, incluso mejores que el fármaco de referencia (itraconazol). Por tanto, 3d y 3e representan importantes núcleos que podrían modificarse para aumentar la actividad antifúngica, siendo excelentes candidatos para estudios complementarios sobre la inhibición de infecciones clínicas producidas por Rhizopus spp.

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Author Biographies

Davir González-Calderón, Universidad Autónoma del Estado de México

Departamento de Química Orgánica, Facultad de Química

Ricardo García-Monroy, Universidad Autónoma del Estado de México

Departamento de Química Orgánica, Facultad de Química

Departamento de Microbiología, Facultad de Química, Universidad Autónoma del Estado de México

Alejandra Ramírez-Villalva, Universidad Autónoma del Estado de México

Departamento de Química Orgánica, Facultad de Química

Departamento de Microbiología, Facultad de Química, Universidad Autónoma del Estado de México

Salvador Mastachi-Loza, Universidad Autónoma del Estado de México

Departamento de Química Orgánica, Facultad de Química

Departamento de Microbiología, Facultad de Química, Universidad Autónoma del Estado de México

José G. Aguirre-de Paz, Universidad Autónoma del Estado de México

Departamento de Química Orgánica, Facultad de Química

Aydee Fuentes-Benítes, Universidad Autónoma del Estado de México

Departamento de Química Orgánica, Facultad de Química

Carlos González-Romero, Universidad Autónoma del Estado de México

Departamento de Química Orgánica, Facultad de Química

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2021-02-22

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Vol. 65 No. 2 (2021): Regular Issue

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