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. 2024 Jun 16;29(12):2866.
doi: 10.3390/molecules29122866.

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

Anna Laskowska  1 , Agata J Pacuła-Miszewska  1 , Magdalena Obieziurska-Fabisiak  1 , Aneta Jastrzębska  2 , Angelika Długosz-Pokorska  3 , Katarzyna Gach-Janczak  3 , Jacek Ścianowski  1
Affiliations

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

Anna Laskowska et al. Molecules. .

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.

Keywords: 2-((2-oxopropyl)selanyl)benzoates; antioxidant activity; antiproliferative activity; pharmacophore.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Examples of ester-type drugs.
Scheme 1
Scheme 1
GPx activity cycle and examples of Sec-type catalysts 5–9.
Scheme 2
Scheme 2
Synthetized β-carbonyl selenides with o-ester groups 10 and 12–24.
Figure 2
Figure 2
Results of the antioxidant activity measurements of 20/21, 10/22 and corresponding Se-derivatives with o-amide group.
Figure 3
Figure 3
The results of DPPH test for tested compounds where TEAC–Trolox equivalent antioxidant capacity (IC50Trolox/IC50 compounds) was calculated.
Figure 4
Figure 4
The IC50 for the DPPH test of 20/21, 10/22 and 23/24 and corresponding Se-derivatives with the o-amide group.
See this image and copyright information in PMC

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