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One-Pot Three-Component Synthesis of a Series of 2-Amino-4-(4-oxo-4H-chromen-3-yl)-5-(2,2,2-trifluoroacetyl)-6-(trifluoromethyl)-4H-pyrans and 2-Amino-4-(4-oxo-4H-chromen-3-yl)-5-(thiophene-2-carbonyl)-6-(trifluoromethyl)-4H-pyrans as Promising Anticancer Agents

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Abstract

Novel functionalized 2-amino-4-(4-oxo-4H-chromen-3-yl)-5-(2,2,2-trifluoroacetyl)-6-(trifluoro­methyl)-4H-pyrans and 2-amino-4-(4-oxo-4H-chromen-3-yl)-5-(thiophene-2-carbonyl)-6-(trifluoromethyl)-4H-pyrans have been synthesized by one-pot three-component reaction of 4-oxo-4H-chromene-3-carbaldehyde with three active methylene cyanoacetic acid derivatives and 1,1,1,5,5,5-hexafluoropentane-2,4-dione or 1,1,1-tri­fluoro-5-(thiophen-2-yl)pentane-2,4-dione in distilled water at 60–70°C without a catalyst. The described methodology displayed excellent yields and simple workup procedure. The synthesized compounds were assessed for their in vitro anticancer activity against human breast cancer (MCF-7), liver cancer (HepG-2), and colon cancer cell lines (HCT-116). One of the compounds, 2-amino-4-(4-oxo-4H-chromen-3-yl)-5-(2,2,2-trifluoroacetyl)-6-(trifluoromethyl)-4H-pyran-3-carbonitrile, exhibited excellent anticancer activity versus all tested cancer cell lines with IC50 values ranging from 0.7 to 1.4 μg/mL.

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Funding

The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding this work through research groups program under grant number RGP.2/8/43.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, King Khalid University, 61421, Abha, Saudi Arabia

    T. E. Ali & M. A. Assiri

  2. Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, 11711, Cairo, Egypt

    T. E. Ali

  3. Department of Biology, Faculty of Science, King Khalid University, 61421, Abha, Saudi Arabia

    A. A. Shati, M. Y. Alfaifi & S. E. I. Elbehairi

  4. Cell Culture Lab, Egyptian Organization for Biological Products and Vaccines (VACSERA Holding Company), Agouza, 12611, Giza, Egypt

    S. E. I. Elbehairi

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  1. T. E. Ali
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  4. M. Y. Alfaifi
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  5. S. E. I. Elbehairi
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Correspondence to T. E. Ali.

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Ali, T.E., Assiri, M.A., Shati, A.A. et al. One-Pot Three-Component Synthesis of a Series of 2-Amino-4-(4-oxo-4H-chromen-3-yl)-5-(2,2,2-trifluoroacetyl)-6-(trifluoromethyl)-4H-pyrans and 2-Amino-4-(4-oxo-4H-chromen-3-yl)-5-(thiophene-2-carbonyl)-6-(trifluoromethyl)-4H-pyrans as Promising Anticancer Agents. Russ J Org Chem 58, 584–591 (2022). https://doi.org/10.1134/S1070428022040170

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