Synthetic 2-Nitrocinnamates: Investigation of the Antifungal Action against Candida Species

Abstract

Derivatives of cinnamic acid have several pharmacological actions, such as antimicrobial activity. Therefore, in the present study, a series of fourteen alkyl and aryl derivatives from (E)-2-nitrocinnamic acid were obtained using Fischer esterification, nucleophilic substitution with halides, and Mitsunobu reaction. Esters were evaluated for antifungal activity against several strains of Candida spp. using nystatin as a positive control. Among the synthetic derivatives obtained, nine are compounds unprecedented in the literature. The characterization of chemical structures was carried out using the techniques of IR, 1H-NMR and 13C-NMR spectroscopy, and high-resolution mass spectrometry. Isopropyl 2-nitrocinnamate (4) was the compound that showed the best antifungal activity (MIC = 513.52 μM) against all fungal strains, followed by compound perillyl 2-nitrocinnamate (14) with MIC = 390.99–781.98 μM.