Work

Synthesis and Antioxidant and Antimicrobial Properties of β-Hydroxy Sulfides, Sulfoxides, and Sulfones Derived from Cardanol and Glycerol Derivatives

Year: 2020

Type: article

Abstract: Natural and synthetic sulfur-bearing organic compounds have many applications in medicinal chemistry.This article reports the preparation of amphiphilic β-hydroxy sulfides, sulfoxides, and sulfones derived from cardanol and glycerol.Thiolysis of cardanol epoxide 3 with various thiols (4a-4j) in ethanol or water yielded the corresponding β-hydroxy sulfides 5a-5j (61-95%).Treatment with 30% H 2 O 2 in acetic acid at ambient temperature completely converted these products into β-hydroxy sulfoxides 6a-6j and sulfones 7a, 7c-7f, 7h-7j.The synthesized compounds were characterized by 1 H nuclear magnetic resonance (NMR), 13 C NMR, high-resolution mass spectroscopy (HRMS) and performed the in vitro evaluation antimicrobial activities against standard strains of Staphylococcus aureus and Escherichia coli.Compounds 5a, 5d-5f, and 5h-5j proved moderately active against S. aureus.None of the compounds were active against E. coli.β-Hydroxy-sulfides 5a-5j were also evaluated for antioxidant properties but failed to exhibit significant activity.

Source: Journal of the Brazilian Chemical Society

DOI: 10.21577/0103-5053.20200136

Authors: Suély Copini, Ana Micheletti, Dênis de Lima, Roberto Gomes, Alisson Meza, Adilson Beatriz

Institutions: Universidade Federal de Mato Grosso do Sul, Instituto Federal de Educação Ciência e Tecnologia do Mato Grosso do Sul, North Dakota State University, Centro Universitário Anhanguera

Language: English

Topic: Sulfur-Based Synthesis Techniques

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

SDG: Good health and well-being

Open Access status: gold

Estimated APC paid: $275