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

Abstract

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, 1H NMR, 13C 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).

Synthesis and Biological Evaluation of Triazole linked Thiazolidenone Glycosides

“…Following the successful introduction of antimicrobial and nematicidal agents, inspired by the biological profile of triazoles, thiazolidenones, and in the continuation of our work on biologically active heterocycles, [27][28][29][30][31][32][33][34][35][36][37][38][39] we have developed a series of novel triazole linked thiazolidenone derivatives, and evaluated their nematicidal activity along with antibacterial activity.…”

Synthesis, Nematicidal and Antifungal Properties of Hybrid Heterocyclics

“…Following the successful introduction of antimicrobial and nematicidal agents, inspired by the biological profile of triazoles, thiazolidinones, pyrazoles and their increasing importance in pharmaceutical and biological fields and in continuation of our work on biologically active molecules [34][35][36][37][38][39][40][41][42][43][44][45][46][47][48] and in order to enhance the biological activity of triazoles, thiazolidinones and pyrazole moieties, it was thought to be of interest to accomodate triazole, thiazolidinones and pyrazole moieties in single molecular framework. In this article we report the synthesis of a new class of hybrid heterocycles 10a-g in good yields…”

Microwave-assisted Synthesis of Hybrid Heterocycles as Potential Anticancer Agents

“…Following the successful introduction of triazoles and thiazolidinones, microwave-assisted MCR reactions, inspired by the biological profile of triazoles, thiazolidinones, and in the continuation of our work on biologically active heterocycles [18][19][20][21][22][23][24][25][26][27][28][29] we have developed a series of novel triazole-linked thiazolidenone derivatives, we have investigated the application of microwave irradiation for the synthesis of our hybrid molecules and evaluated their anticancer activity.…”