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Synthesis and evaluation of p-N,N-dialkyl substituted chalcones as anti-cancer agents

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Abstract

Several new N,N-dialkyl substituted chalcones (chalconoids or benzylideneacetophenones) have been synthesized via the condensation of corresponding N,N-dialkylbenzaldehyde with various aryl methyl ketones. All the chalcones have been synthesized from readily available and cheap starting materials under environmentally benign conditions in very high yields without work up and column chromatographic purification. Synthesized compounds have been tested for their biological activity against pathogenic microorganisms such as Escherichia coli, Bacillus subtilis, and Mycobacterium smegmatis. Anti-cancer activity of these compounds has also been tested against multiple myeloma (RPMI-8226) and human mammary adenocarcinoma (MCF-7) cell lines. The most hydrophilic molecules 23 and 24 showed very good anti-cancer activity against MCF-7 cell lines at low micro-molar concentrations. All the compounds have also been evaluated for their activity against Beta-secretase 1 enzyme. One of the synthesized compounds showed Beta-secretase 1 enzyme inhibition activity at micro-molar concentration.

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Acknowledgments

We thank Dr. Venkatram Mereddy (University of Minnesota Duluth) for providing facilities and valuable suggestions.

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN, 55812, USA

    Grady Nelson, Mohammad A. Alam, Tyler Atkinson, Shirisha Gurrapu, J. Sravan Kumar, Chris Bicknese, Joseph L. Johnson & Michael Williams

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  1. Grady Nelson
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  2. Mohammad A. Alam
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  3. Tyler Atkinson
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  4. Shirisha Gurrapu
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  5. J. Sravan Kumar
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  7. Joseph L. Johnson
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  8. Michael Williams
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Correspondence to Mohammad A. Alam.

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Nelson, G., Alam, M.A., Atkinson, T. et al. Synthesis and evaluation of p-N,N-dialkyl substituted chalcones as anti-cancer agents. Med Chem Res 22, 4610–4614 (2013). https://doi.org/10.1007/s00044-013-0469-8

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  • DOI: https://doi.org/10.1007/s00044-013-0469-8

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