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Medicinal Chemistry Research

, Volume 22, Issue 12, pp 5934–5939 | Cite as

Solvent-free, green and efficient synthesis of pyrano[4, 3-b]pyrans by grinding and their biological evaluation as antitumor and antioxidant agents

  • Deepika Rajguru
  • Balwant S. KeshwalEmail author
  • Shubha Jain
Original Research

Abstract

A facile, green, and efficient method has been developed for the synthesis of pyrano[4, 3-b]pyrans via a one-pot reaction of aromatic aldehydes, malononitrile, and 4-hydroxy-6-methyl-pyran-2-one in the presence of ammonium acetate under solvent-free conditions using grinding method. The experimental simplicity, short reaction time, easy work-up, avoidance of organic solvents, and utilization of an inexpensive and readily available catalyst make this new methodology practical and economically attractive. The antitumor activity of the compounds was tested against human breast cancer cell line MCF-7. Compounds 4l, 4o, and 4p showed good cytotoxic activity comparable with standard drug Doxorubicin. On the other hand, compounds 4q and 4r exhibited potent growth inhibitory activity. Furthermore, the synthesized compounds were screened for in vitro antioxidant activity by DPPH assay. All the compounds assayed showed moderate to good free radical scavenging activity.

Keywords

Pyrano[4, 3-b]pyrans Green chemistry One-pot synthesis Grinding Solvent-free Cytotoxicity Antioxidant activity 

Notes

Acknowledgments

The authors are thankful to the authorities of Deshpande Laboratories Pvt. Ltd., Bhopal (M.P.), India and Pinnacle Biomedical Research Institute, Bhopal (M.P.), India for the studies of biological activities. The authors also thank The Director, SAIF, Panjab University, Chandigarh for NMR and MS spectral data.

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Deepika Rajguru
    • 1
  • Balwant S. Keshwal
    • 1
    Email author
  • Shubha Jain
    • 1
  1. 1.School of Studies in ChemistryVikram UniversityUjjainIndia

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