Silicon Incorporated Morpholine Antifungals: Design, Synthesis, and Biological Evaluation

ACS Med Chem Lett. 2015 Sep 22;6(11):1111-6. doi: 10.1021/acsmedchemlett.5b00245. eCollection 2015 Nov 12.

Abstract

Known morpholine class antifungals (fenpropimorph, fenpropidin, and amorolfine) were synthetically modified through silicon incorporation to have 15 sila-analogues. Twelve sila-analogues exhibited potent antifungal activity against different human fungal pathogens such as Candida albicans, Candida glabrata, Candida tropicalis, Cryptococcus neoformans, and Aspergillus niger. Sila-analogue 24 (fenpropimorph analogue) was the best in our hands, which showed superior fungicidal potential than fenpropidin, fenpropimorph, and amorolfine. The mode of action of sila-analogues was similar to morpholines, i.e., inhibition of sterol reductase and sterol isomerase enzymes of ergosterol synthesis pathway.

Keywords: Antifungal drugs; Candida albicans; ergosterol biosynthesis; morpholines; sila-analogues.