Antimicrobial activity of allylic thiocyanates derived from the Morita-Baylis-Hillman reaction

Abstract

Bacterial resistance to commonly used antibiotics has been recognized as a significant global health issue. In this study, we carried out the screening of a family of allylic thiocyanates for their action against a diversity of bacteria and fungi with a view to developing new antimicrobial agents. Allylic thiocyanates bearing halogenated aryl groups, which were readily obtained in two steps from the Morita-Baylis-Hillman adducts, showed moderate-to-high activity against selective pathogens, including a methicillin-resistant S. aureus (MRSA) strain. In particular cases, methyl (Z)-3-(2,4-dichlorophenyl)-2-(thiocyanomethyl)-2-propenoate exhibited antimicrobial activity comparable to the reference antibiotic Imipenem.

Nanoemulsion Improves the Antifungal Activity of Allylic Thiocyanates against Yeasts and Filamentous Pathogenic Fungi

“…Previous data showed that compound 11 exhibited moderate‐to‐good activity against C. albicans (12.5 μmol L −1 ) and C. tropicalis (25 μmol L −1 ); these findings corroborate to our results. Furthermore, compounds 8 , 9 , 11 and 14 inhibited MRSA growth, and thus demonstrated a broad spectrum of action against fungi and bacteria.…”

“…Previous data showed that compound 11 exhibited moderate‐to‐good activity against C. albicans (12.5 μmol L −1 ) and C. tropicalis (25 μmol L −1 ); these findings corroborate to our results. Furthermore, compounds 8 , 9 , 11 and 14 inhibited MRSA growth, and thus demonstrated a broad spectrum of action against fungi and bacteria. Compound 11 and bromo‐substituted analogues 8 and 9 exhibited promising antitubercular activity against replicating and non‐replicating forms of Mtb H 37 Rv (MIC 0.25 μmol L −1 ) with relatively low toxicity toward VERO cells .…”

“…Chain elongation was also deleterious to activity (see the cinnamoyl derivative ‐ compound 15 ; Supporting Information, Table S1) as well as the simultaneous presence of two substituents at the aromatic ring, such as in compounds 12 and 13 . Hence, our screening of the thiocyanates 1–15 against the present panel of fungi correlated with previous results for these compounds towards Mtb and bacteria, allowed us to select compound 11 as the best lead for further evaluation to develop a new broad spectrum drug and NE to treat microbial skin infections. Therefore, its mechanism of antifungal action, anti‐inflammatory capacity and toxicity were determined.…”

“…Allylic thiocyanates showed moderate‐to‐high activity against methicillin‐resistant Staphylococcus aureus (MRSA), Mycobacterium tuberculosis (Mtb), human cancer cells and other targets . Therefore, we present the antifungal activity of functionalised allylic thiocyanates derived from the Morita‐Baylis‐Hillman reaction, as well as the toxicity and anti‐inflammatory properties of this collection of sulphur‐containing derivatives.…”

Allylic Selenocyanates as New Agents to Combat Fusarium Species Involved with Human Infections

“…It was shown that a piperidine isoselenocyanate derivative is the most active among its isosters against selected fungi, including Fusarium culmorum . Furthermore, related thiocyanates exhibit a variety of biological properties,, including antibacterial activity against Mycobacterium tuberculosis and methicillin‐resistant Staphylococcus aureus (MRSA) . These facts motivate the investigation of allylic organoselenium compounds as antifungal agents.…”