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Bioorganic & Medicinal Chemistry Letters
Volume 30 (17), 2020, 127413

Synthesis of novel lignan-like compounds and their antimicrobial activity

Immacolata Tufanoa,b, Elisabetta Buomminoc, Maria Rosaria Iescea, Anna De Filippisc, Paolo Griecoc, Francesca Lemboc, Marina Della Grecaa

Department of Chemical Sciences, University Federico II of Naples, Complesso Universitario Monte S. Angelo, via Cinthia, 4, 80126 Naples, Italy.

Abstract

Herein we report the preparation of 3,4-dibenzylfurans and some oxidized derivatives with lignan backbone. The compounds were prepared using the Friedel-Crafts reaction with BF3 etherate as catalyst, demethylation with iodocyclohexane, acetylation and oxidation reactions. The antimicrobial activity was evaluated through their capacity to inhibit the growth of Gram positive and Gram negative bacteria, and of the yeast Candida albicans. Among ten products assayed four furans displayed a good antimicrobial activity against Staphylococcus aureusSepidermidis and Calbicans; on the contrary, none of the compounds were active against Pseudomonas aeruginosa. One of them inhibited the growth of SaureusSepidermidis (biofilm producer strain) and Calbicans at 16 μg/mL, showing a bactericidal activity already after one hour of treatment. In summary, the results suggest a possible use of these derivatives for general disinfection practices or antimicrobial agents in cosmesis skin-care.

Keywords: Lignans, 3,4-Dibenzylfurans, Demethylation, Oxidation, Friedel–Crafts alkylation, Antimicrobial activity.

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