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

Suély Copini,Dênis De Lima,Roberto Gomes,Adilson Beatriz,Alisson Meza,Ana Micheletti

doi:10.21577/0103-5053.20200136

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% H2O2 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 1H nuclear magnetic resonance (NMR), 13C 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.

Highlights

Sulfur-bearing organic compounds are ubiquitous in nature
Synthesis of β-hydroxy sulfides, sulfoxides, and sulfones derived from cardanol and glycerol
Synthesis of β-hydroxy sulfides 5a-5j A 2 mL volume of 0.03 M sodium hydroxide in ethanol was added to an ethanol solution (2 mL) of 1 mmol cardanol epoxide 311 and 1.0 mmol thiol at ambient temperature and the mixture stirred at 30 °C for 2 h

Summary

Introduction

Sulfur-bearing organic compounds are ubiquitous in nature. Because sulfur is, after chlorine, the most abundant element in sea water, organosulfur compounds are typically isolated from marine organisms.[1,2] In the molecular architecture of these natural compounds, sulfur can be a component of various functional groups, exhibiting differing states of oxidation, as in thiols, sulfides (acyclic or heterocyclic), disulfides, sulfoxides, and sulfonates.[2,3] Antioxidant, antimicrobial, anti-inflammatory, antitumor, anti-HIV, and calcium-channel-antagonist activities make natural and synthetic organic compounds containing sulfur useful for numerous applications in medicinal chemistry.[4] β-Hydroxy sulfides are constituents of several biologicallyIn line with our interest to explore the Brazilian biomass for substances of special structural and chemical interest, our research group has been investigating the potential of cardanol (1) and glycerol (2) to yield hybrid compoundsSynthesis and Antioxidant and Antimicrobial Properties of β-Hydroxy Sulfides, Sulfoxides, and SulfonesJ. Sulfur-bearing organic compounds are ubiquitous in nature. After chlorine, the most abundant element in sea water, organosulfur compounds are typically isolated from marine organisms.[1,2] In the molecular architecture of these natural compounds, sulfur can be a component of various functional groups, exhibiting differing states of oxidation, as in thiols, sulfides (acyclic or heterocyclic), disulfides, sulfoxides, and sulfonates.[2,3] Antioxidant, antimicrobial, anti-inflammatory, antitumor, anti-HIV, and calcium-channel-antagonist activities make natural and synthetic organic compounds containing sulfur useful for numerous applications in medicinal chemistry.[4] β-Hydroxy sulfides are constituents of several biologically. In line with our interest to explore the Brazilian biomass for substances of special structural and chemical interest, our research group has been investigating the potential of cardanol (1) and glycerol (2) to yield hybrid compounds.

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Results

Conclusion