Chemoselective Preparation of New Families of Phenolic-Organoselenium Hybrids—A Biological Assessment

Abstract

Being aware of the enormous biological potential of organoselenium and polyphenolic compounds, we have accomplished the preparation of novel hybrids, combining both pharmacophores in order to obtain new antioxidant and antiproliferative agents. Three different families have been accessed in a straightforward and chemoselective fashion: carbohydrate-containing N-acylisoselenoureas, N-arylisoselenocarbamates and N-arylselenocarbamates. The nature of the organoselenium framework, number and position of phenolic hydroxyl groups and substituents on the aromatic scaffolds afforded valuable structure–activity relationships for the biological assays accomplished: antioxidant properties (antiradical activity, DNA-protective effects, Glutathione peroxidase (GPx) mimicry) and antiproliferative activity. Regarding the antioxidant activity, selenocarbamates 24–27 behaved as excellent mimetics of GPx in the substoichiometric elimination of H2O2 as a Reactive Oxygen Species (ROS) model. Isoselenocarbamates and particularly their selenocarbamate isomers exhibited potent antiproliferative activity against non-small lung cell lines (A549, SW1573) in the low micromolar range, with similar potency to that shown by the chemotherapeutic agent cisplatin (cis-diaminodichloroplatin, CDDP) and occasionally with more potency than etoposide (VP-16).

Polyphenol-Rich Extracts from Agroindustrial Waste and Byproducts: Results and Perspectives According to the Green Chemistry and Circular Economy

“…More recently, HTyr has been employed as a starting material for the synthesis of a panel of selenocarbamates via direct nucleophilic coupling between the phenolic derivative and the selenocumulene (Scheme ). Due to the strong antioxidant properties of selenium-containing compounds, products obtained this way showed significant in vitro antioxidant activity alongside antiproliferative activity on tumor cell lines …”

“…Due to the strong antioxidant properties of selenium-containing compounds, products obtained this way showed significant in vitro antioxidant activity alongside antiproliferative activity on tumor cell lines. 126 Compared with HTyr, the derivatization of Ole has been scarcely investigated. The primary hydroxyl group in the structure is the most reactive position for selective functionalization.…”

Selenium-Containing (Hetero)Aryl Hybrids as Potential Antileishmanial Drug Candidates: In Vitro Screening against L. amazonensis

“…The strategic integration of selenium (Se) atoms into organic frameworks offers a promising avenue for the creation of enhanced, disease-specific compounds. Organoselenium compounds are renowned for their diverse pharmacological properties [9][10][11][12][13][14][15][16][17][18][19][20]. Furthermore, the biocompatibility, minimal toxicity, and chemical versatility of selenium have spurred the development of a diverse range of Se-based pharmaceuticals.…”

Selenium-Containing (Hetero)Aryl Hybrids as Potential Antileishmanial Drug Candidates: In vitro Screening Against L. amazonensis

“…The strategic integration of selenium (Se) atoms into organic frameworks offers a highly auspicious avenue for the creation of enhanced, disease-specific compounds. Organoselenium compounds are renowned for their diverse pharmacological properties [9][10][11][12][13][14][15][16][17][18][19][20]. Furthermore, the biocompatibility, minimal toxicity, and chemical versatility of selenium have spurred the development of a diverse range of Se-based pharmaceuticals.…”