Synthesis of a New Class of β-Carbonyl Selenides Functionalized with Ester Groups with Antioxidant and Anticancer Properties

Synthesis of a New Class of β-Carbonyl Selenides Functionalized with Ester Groups with Antioxidant and Anticancer Properties—Part II

Published:2024-06-16 Issue:12 Volume:29 Page:2866
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Laskowska Anna¹,Pacuła-Miszewska Agata J.¹^ORCID,Obieziurska-Fabisiak Magdalena¹,Jastrzębska Aneta²^ORCID,Długosz-Pokorska Angelika³,Gach-Janczak Katarzyna³^ORCID,Ścianowski Jacek¹^ORCID

Affiliation:

1. Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Torun, Poland

2. Department of Analytical Chemistry and Applied Spectroscopy, Faculty of Chemistry, Nicolaus Copernicus University in Torun, 7 Gagarin Street, 87-100 Torun, Poland

3. Department of Biomolecular Chemistry, Faculty of Medicine, Medical University of Lodz, 6/8 Mazowiecka Street, 92-215 Lodz, Poland

Abstract

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.

Funder

Medical University of Lodz

Publisher

MDPI AG

Link

https://www.mdpi.com/1420-3049/29/12/2866/pdf

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