Synthesis of a New Class of <i>β</i>-Carbonyl Selenides Functionalized with Ester Groups with Antioxidant and Anticancer Properties—Part II
Anna Laskowska,
Agata J. Pacuła-Miszewska,
Magdalena Obieziurska-Fabisiak,
Aneta Jastrzębska,
Angelika Długosz-Pokorska,
Katarzyna Gach-Janczak,
Jacek Ścianowski
Affiliations
Anna Laskowska
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland
Agata J. Pacuła-Miszewska
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland
Magdalena Obieziurska-Fabisiak
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland
Aneta Jastrzębska
Department of Analytical Chemistry and Applied Spectroscopy, Faculty of Chemistry, Nicolaus Copernicus University in Torun, 7 Gagarin Street, 87-100 Torun, Poland
Angelika Długosz-Pokorska
Department of Biomolecular Chemistry, Faculty of Medicine, Medical University of Lodz, 6/8 Mazowiecka Street, 92-215 Lodz, Poland
Katarzyna Gach-Janczak
Department of Biomolecular Chemistry, Faculty of Medicine, Medical University of Lodz, 6/8 Mazowiecka Street, 92-215 Lodz, Poland
Jacek Ścianowski
Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland
A series of phenyl β-carbonyl selenides with o-ester functionality substituted on the oxygen atom with chiral and achiral alkyl groups was synthesized. All compounds are the first examples of this type of organoselenium derivatives with an ester substituent in the ortho position. The obtained derivatives were tested as antioxidants and anticancer agents to see the influence of an ester functionality on the bioactivity of β-carbonyl selenides by replacing the o-amide group with an o-ester group. The best results as an antioxidant agent were observed for O-((1R,2S,5R)-(−)-2-isopropyl-5-methylcyclohexyl)-2-((2-oxopropyl)selanyl)benzoate. The most cytotoxic derivative against breast cancer MCF-7 cell lines was O-(methyl)-2-((2-oxopropyl)selanyl)benzoate and against human promyelocytic leukemia HL-60 was O-(2-pentyl)-2-((2-oxopropyl)selanyl)benzoate.
