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An Efficient, Eco-Friendly Synthesis of Pyran Annulated Indole Analogs under Conventional Heating and Microwave Irradiation, and Their Anticancer and Antioxidant Activity

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Abstract

A rapid, facile, green, eco-friendly, cost effective, and efficient method for the synthesis of pyran annulated indole analogs via one-pot, three components reaction is developed. According to the developed method 2,5-disubstituted-1H-indol-3-carboxaldehyde, malononitrile and various phenols react under MW assisted solvent-free conditions. These compounds can be also prepared under a conventional method that is characterized by some disadvantages in comparison with the above approach. Structures of products are confirmed by FT-IR, 1H and 13C NMR, and mass spectral data. The in vitro antioxidant and cytotoxic activities of the products are evaluated against three tumor cell lines and discussed in terms of structure―activity analysis. Among the screened compounds 3d, 4a, 4b, 5a, and 5b exhibit excellent antioxidant activity. Compounds 4b, 5a, and 5b demonstrate strong cytotoxic activity.

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References

  1. Rathod, A.S., Godipurge, S.S., and Biradar, J.S., Russ. J. Gen. Chem., 2018, vol. 88 p. 1238. doi 10.1134/S1070363218060324

    Article  CAS  Google Scholar 

  2. De-Hoz, A., Díaz-Ortiz, A., Moreno, A., and Herrero, M.A., Comb. Chem. High. Throughput Screen., 2007, vol. 10, p. 877. doi 10.2174/138620707783220347

    Article  Google Scholar 

  3. Sasidhar, B.S., and Biradar, J.S., Med. Chem. Res., 2013, vol. 22, p. 3518. doi 10.1007/s00044-012-0370-x

    Article  CAS  Google Scholar 

  4. Biradar, J.S., and Sashidhar, B.S., Eur. J. Med. Chem., 2011, vol. 46, p. 6112. doi 10.1016/j.ejmech.2011.10.004

    Article  CAS  PubMed  Google Scholar 

  5. Lea, A.J., Lancet, 1966, vol. 2, p. 332. doi 10.1016/s0140-6736(66)92615-8

    Article  CAS  PubMed  Google Scholar 

  6. Cuzzocrea, S., Riley, D.P., Caputi, A.P., and Salvemini, D., Pharmacol. Rev., 2001, vol. 53, p.135.

    CAS  PubMed  Google Scholar 

  7. Wu, Y.S., Coumar, M.S., and Chang, J.Y., et al., J. Med. Chem., 2009, vol. 52, no. 15, p. 4941. doi 10.1021/jm900060s

    Article  CAS  PubMed  Google Scholar 

  8. Pojarova, M., Kaufmann, D., Gastpar, R., and Nishino, T., Reszka, P., Bednarski, P.J., and von Angerer, E., Bioorg. Med. Chem., 2007, vol. 15, p. 7368. doi 10.1016/j.bmc.2007.07.046

    Article  CAS  PubMed  Google Scholar 

  9. Anil, R., Shivakumar, G., and Jaiprakash, B., Int. J. Pharm. Pharm. Sci., 2017, vol. 9, no. 12, p. 233. doi 10.22159/ijpps.2017v9i12.21970

    Article  CAS  Google Scholar 

  10. Anil, R., Shivakumar, G., and Jaiprakash, B., Asian J. Pharm. Pharmacol., 2017, vol. 3, no. 6, p.229.

    Google Scholar 

  11. Buyukbingol, E., Suzen, S., and Klopman, G., Il Farmaco, 1994, vol. 49, p.443.

    CAS  PubMed  Google Scholar 

  12. Suzen, S., and Buyukbingol, E., Il Farmaco, 1998, vol. 53, p. 525. doi 10.1016/S0014-827X(98)00053-6

    Article  CAS  PubMed  Google Scholar 

  13. Zeynep, A.A., Tulay, C., and Sibel, S., Med. Chem. Res., 2005, vol. 14, no. 3, p. 169.

    Article  Google Scholar 

Download references

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Authors and Affiliations

  1. Central Research Laboratory, Department of Chemistry, Gulbarga University, Kalaburagi, Karnataka, 585106, India

    A. S. Rathod & J. S. Biradar

Authors
  1. A. S. Rathod
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  2. J. S. Biradar
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Correspondence to A. S. Rathod.

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Rathod, A.S., Biradar, J.S. An Efficient, Eco-Friendly Synthesis of Pyran Annulated Indole Analogs under Conventional Heating and Microwave Irradiation, and Their Anticancer and Antioxidant Activity. Russ J Gen Chem 88, 2190–2196 (2018). https://doi.org/10.1134/S1070363218100262

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  • DOI: https://doi.org/10.1134/S1070363218100262

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