Design, synthesis, synergistic antimicrobial activity and cytotoxicity of 4-aryl substituted 3,4-dihydropyrimidinones of curcumin

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Abstract

3,4-Dihydropyrimidinones of curcumin were synthesized in excellent yield by multi-component one-pot condensation of curcumin, substituted aromatic aldehydes and urea/thiourea under solvent free conditions using SnCl2·2H2O catalyst. All the synthesized compounds have been characterized by IR, 1H NMR, 13C NMR, Mass spectra as well as elemental analyses. The synthesized compounds 4an were evaluated for their synergistic antimicrobial (antibacterial and antifungal) activity against bacteria and fungi. Zone of inhibition was measured by adopting disc diffusion method. In vitro minimum inhibitory concentrations were measured using broth microdilution and food poisoning method. In addition to this in vitro cytotoxicity of synthesized compounds against three human cancer lines Hep-G2, HCT-116 and QG-56 were also evaluated. Most of the compounds showed interesting antimicrobial and cytotoxic activity as compared to curcumin, that is, the compounds derived from 2-hydroxy benzaldehyde, 4-hydroxy benzaldehyde and 4-hydroxy-3-methoxy benzaldehyde showed the highest biological activity as compared to other compounds.

Graphical abstract

3,4-Dihydropyrimidinones of curcumin were synthesized in excellent yield by multi-component one-pot condensation of curcumin, substituted aromatic aldehydes and urea/thiourea under solvent free conditions using SnCl2·2H2O catalyst.

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Acknowledgments

The authors are indebted to Madhya Pradesh Council of Science and Technology, Bhopal for financial support (Grant No. 4468/CST/R&D/2010), the Director, Defense Research & Development Establishment, Jhansi Road, Gwalior-474 002 (M.P.), for carrying out biological activity of the synthesized compounds.

References and notes (29)

  • P. Cornago et al.

    Tetrahedron

    (2008)
  • S.K. Abraham et al.

    Mutat. Res.

    (1993)
  • G. Liang et al.

    Eur. J. Med. Chem.

    (2009)
  • M.K. Kim et al.

    Bioorg. Med. Chem.

    (2011)
  • S. Mishra et al.

    Bioorg. Med. Chem.

    (2008)
  • Y. Shukla et al.

    Mutat. Res.

    (2002)
  • A.B. Hegge et al.

    J. Pharma. Sci.

    (2011)
  • N.S. Gupta et al.

    J. Pharma. Sci.

    (2011)
  • M. Ashok et al.

    Eur. J. Med. Chem.

    (2007)
  • R. Feng et al.

    J. Biol. Chem.

    (2005)
  • L. Lin et al.

    Bioorg. Med. Chem.

    (2006)
  • B.K. Banik et al.

    Tetrahedron Lett.

    (2007)
  • A. Manvar et al.

    Bioorg. Med. Chem. Lett.

    (2011)
  • W. Wichitnithad et al.

    Phytochem. Anal.

    (2009)
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