Synthesis and <i>in vitro</i> study of a new class of methylene‐bis‐4,6‐diarylbenzo[<i>d</i>]isoxazoles as potential antifungal agents

Abstract

Abstract magnified image A new class of methylene‐bis‐4,6‐diarylbenzo[ d ]isoxazoles 8a , 8b , 8c , 8d , 8e , 8f , 8g , 8h , 8i was synthesized by the reaction of methylene‐bis‐aryl‐6‐hydroxymethylene‐2‐cyclohexenone 6 with hydroxylamine hydrochloride, followed by aromatization with DDQ. Chemical structures of the newly synthesized compounds were elucidated by their IR, 1 H NMR, 13 C NMR, MS, and elemental analyses. Furthermore, all the compounds were screened for their antifungal activity against various fungi and compared with their monomeric compounds. Among the synthesized compounds, 8b , 8g , and 8i were found to be the most active against Candida albicans (ATCC 10231), Aspergillus fumigatus (HIC 6094), Trichophyton rubrum (IFO 9185), and Trichophyton mentagrophytes (IFO 40996). It is interesting to note that the compounds 8a , 8g , and 8i showed fungicidal activity toward C. albicans at the concentration of 3.12 μg/mL, which is less than the concentration of standard Amphotericin B. J. Heterocyclic Chem., 46, 497 (2009).