Synthesis and antifungal activity of novel oxazolidin-2-one-linked 1,2,3-triazole derivatives.

Journal: MedChemComm
Published Date: Oct 17, 2017

Abstract

Novel oxazolidin-2-one-linked 1,2,3-triazole derivatives () were synthesized by straightforward and versatile azide-enolate (3 + 2) cycloaddition. The series of compounds was screened for antifungal activity against four filamentous fungi as well as six yeast species of spp. According to their efficiency and breadth of scope, they can be ordered as > > > , especially in relation to the activity displayed against ATCC-34138, ATCC-28592 and ATCC-8690, compounds , and showed excellent activity against (MIC 0.12, 0.25 and 0.12 μg mL, respectively), better than that of itraconazole (MIC 1 μg ml). The activity of compound (MIC = 2 μg mL) was higher than that observed for the standard antifungal drug (MIC = 8 μg mL) against , while compound displayed an excellent antimycotic activity against (MIC = 2 μg mL 4 μg mL for itraconazole). In addition, we describe herein a novel mild and eco-friendly synthetic protocol for obtaining β-ketosulfones (adducts to afford compounds ) from α-brominated carbonyls in an aqueous nanomicellar medium at room temperature.

Authors

  • Alejandra Ramírez-Villalva
    Departamento de Química Orgánica , Facultad de Química , Universidad Autónoma del Estado de México , Paseo Colón/Paseo Tollocan s/n , Toluca , Estado de México 50120 , Mexico . Email: mpagfuentesb@uaemex.mx ; ; Tel: +52 722 217 5109x113.
  • Davir González-Calderón
    Departamento de Química Orgánica , Facultad de Química , Universidad Autónoma del Estado de México , Paseo Colón/Paseo Tollocan s/n , Toluca , Estado de México 50120 , Mexico . Email: mpagfuentesb@uaemex.mx ; ; Tel: +52 722 217 5109x113.
  • Roxana I Rojas-García
    Departamento de Química Orgánica , Facultad de Química , Universidad Autónoma del Estado de México , Paseo Colón/Paseo Tollocan s/n , Toluca , Estado de México 50120 , Mexico . Email: mpagfuentesb@uaemex.mx ; ; Tel: +52 722 217 5109x113.
  • Carlos González-Romero
    Departamento de Química Orgánica , Facultad de Química , Universidad Autónoma del Estado de México , Paseo Colón/Paseo Tollocan s/n , Toluca , Estado de México 50120 , Mexico . Email: mpagfuentesb@uaemex.mx ; ; Tel: +52 722 217 5109x113.
  • Joaquín Tamaríz-Mascarúa
    Departamento de Química Orgánica , Escuela Nacional de Ciencias Biológicas , Instituto Politécnico Nacional , Prol. Carpio y Plan de Ayala , Ciudad de México , 11340 , Mexico.
  • Macario Morales-Rodríguez
    Departamento de Microbiología , Facultad de Química , Universidad Autónoma del Estado de México , Paseo Colón/Paseo Tollocan s/n , Toluca , Estado de México 50120 , Mexico.
  • Nieves Zavala-Segovia
    Centro Conjunto de Investigación en Química Sustentable UAEM-UNAM , Carretera Toluca-Atlacomulco Km 14.5 , Toluca , 52000 , Mexico.
  • Aydeé Fuentes-Benítes
    Departamento de Química Orgánica , Facultad de Química , Universidad Autónoma del Estado de México , Paseo Colón/Paseo Tollocan s/n , Toluca , Estado de México 50120 , Mexico . Email: mpagfuentesb@uaemex.mx ; ; Tel: +52 722 217 5109x113.

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