Green Synthesis of New Coumarins Employing SiO<sub>2</sub>/Fe<sub>3</sub>O<sub>4</sub>@MWCNTs as a Recyclable Catalyst and Evaluation of Antioxidant and Antiproliferative Activity

ABSTRACT This study successfully synthesized coumarins, which belong to a novel class of fused heterocyclic compounds, employing a multicomponent reaction with excellent efficiency. The process utilized 4‐aminocumarin or 4‐hydroxycumarin, 2‐arylidenemalononitrile, and activated acetylenic chemicals in an aqueous solution at room temperature in the presence of MWCNTs@SiO 2 /Fe 3 O 4 as a recyclable catalyst. The synthesized compounds were assessed for their antiproliferative activity against MCF‐7 breast and HCT‐15 colon cancer cell lines using the sulforhodamine B (SRB) assay, as well as their antioxidant effect. Compounds 4c , 4g , and 6d exhibited superior antiproliferative activity compared with other synthesized compounds. The compounds 4c , 4g , and 6d were subjected to UV‐Vis spectroscopy to determine their binding affinity for DNA and BSA. The analysis yielded overall affinity constants K 4c‐DNA = 7.9 × 10 3 M −1 , K 4g‐DNA = 1.1 × 10 4 M −1 , K 6d‐DNA = 4.2 × 10 4 M −1 , K 4c‐BSA = 4.96 × 10 4 M −1 , K 4g‐BSA = 7.54 × 10 4 M −1 , and K 6d‐BSA = 6.47 × 10 4 M −1 . Our research results could offer fresh data demonstrating the correlation between the chemical composition and the ability of these novel coumarin analogs to inhibit cancer growth. The synthesis of fused coumarins exhibited various beneficial characteristics, such as fast reactions, high yields of the end product, and easy isolation of the catalyst and product from the reaction mixture.

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Publication Details

Journal
Applied Organometallic Chemistry
Published
2024-11-18
DOI
https://doi.org/10.1002/aoc.7888
Citations
4
Primary Topic
Multicomponent Synthesis of Heterocycles
Type
article
Field-Weighted Citation Impact
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article

Green Synthesis of New Coumarins Employing SiO2/Fe3O4@MWCNTs as a Recyclable Catalyst and Evaluation of Antioxidant and Antiproliferative Activity

Zinatossadat Hossaini, Fatemeh Sheikholeslami‐Farahani, Ashraf Sadat Shahvelayati, Mahsa Hojjati
4 citations
Applied Organometallic Chemistry
Multicomponent Synthesis of Heterocycles
1.00
article

Green Synthesis of New Coumarins Employing SiO2/Fe3O4@MWCNTs as a Recyclable Catalyst and Evaluation of Antioxidant and Antiproliferative Activity

Zinatossadat Hossaini, Fatemeh Sheikholeslami‐Farahani, Ashraf Sadat Shahvelayati, Mahsa Hojjati
article en
4 citations

Abstract

ABSTRACT This study successfully synthesized coumarins, which belong to a novel class of fused heterocyclic compounds, employing a multicomponent reaction with excellent efficiency. The process utilized 4‐aminocumarin or 4‐hydroxycumarin, 2‐arylidenemalononitrile, and activated acetylenic chemicals in an aqueous solution at room temperature in the presence of MWCNTs@SiO 2 /Fe 3 O 4 as a recyclable catalyst. The synthesized compounds were assessed for their antiproliferative activity against MCF‐7 breast and HCT‐15 colon cancer cell lines using the sulforhodamine B (SRB) assay, as well as their antioxidant effect. Compounds 4c , 4g , and 6d exhibited superior antiproliferative activity compared with other synthesized compounds. The compounds 4c , 4g , and 6d were subjected to UV‐Vis spectroscopy to determine their binding affinity for DNA and BSA. The analysis yielded overall affinity constants K 4c‐DNA = 7.9 × 10 3 M −1 , K 4g‐DNA = 1.1 × 10 4 M −1 , K 6d‐DNA = 4.2 × 10 4 M −1 , K 4c‐BSA = 4.96 × 10 4 M −1 , K 4g‐BSA = 7.54 × 10 4 M −1 , and K 6d‐BSA = 6.47 × 10 4 M −1 . Our research results could offer fresh data demonstrating the correlation between the chemical composition and the ability of these novel coumarin analogs to inhibit cancer growth. The synthesis of fused coumarins exhibited various beneficial characteristics, such as fast reactions, high yields of the end product, and easy isolation of the catalyst and product from the reaction mixture.

Applied Organometallic ChemistryVol. 39(3)
Islamic Azad University, Tehran (IR), Islamic Azad University, Firoozkooh Branch (IR), University of Georgia (GE), Qaemshahr Islamic Azad University (IR)
Openalex Percentile: Top 26%
Multicomponent Synthesis of Heterocycles
1.00
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