Synthesis and antifungal activities of new fluconazole analogues with azaheterocycle moiety

A series of fluconazole analogues 5–20 incorporating azaindole and indole moieties were prepared using oxirane intermediates synthesized under microwave irradiation. All of the compounds were evaluated in vitro against two clinically important fungi, Candida albicans and Aspergillus fumigatus. Four derivatives 6, 13, 14 and 18 exerted high antifungal activity against C. albicans with MIC80 values 3- to 28-fold lower than that of fluconazole.

Graphical abstractA series of fluconazole analogues 5–20 incorporating azaindole and indole moieties were prepared using oxirane intermediates synthesized under microwave irradiation. All of the compounds were evaluated in vitro against two clinically important fungi, Candida albicans and Aspergillus fumigatus. Four 2,4-dichlorophenyl derivatives 6, 13, 14 and 18 exerted high antifungal activity against C. albicans with MIC80 values 3- to 28-fold lower than that of fluconazole.Figure optionsDownload full-size imageDownload as PowerPoint slide