Skip to main content
Log in

Synthesis and synergistic, additive inhibitory effects of novel spiro derivatives against ringworm infections

  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

An environmentally benign solvent free synthesis of various spiro-1,4-dihydropyridines (1,4-DHPs) incorporating 2-oxindole/piperidines is performed in 5–8 min with reasonable purity in 80–90% yield under microwave irradiation using montmorillonite KSF as an inorganic solid support. The reaction is found to be general with respect to various cyclic carbonyl compounds, e.g. cyclohexanone, substituted indole-2,3-dione, and piperidinone derivatives. In our study, these compounds were also found effective against dermatophytes and other fungal organisms. Our results suggest that novel spiro derivatives can be used for the treatment of dermatophytosis or ringworm infections.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Kazemizadeh, A.R. and Ramazani, A., Arkivoc, 2008, vol. 15, pp. 159–165.

    Article  Google Scholar 

  2. Stevenson, P.J., Nieuwenhuyzen, M., and Osborne, D., Arkivoc, 2007, vol. 11, pp. 129–144.

    Google Scholar 

  3. Willy, B. and Müller, T.J.J., Arkivoc, 2008, vol. 1, pp. 195–208.

    Article  Google Scholar 

  4. Weber, L., Ligen, K., and Amstetter, M., Synlett, 1999, pp. 366–374.

    Google Scholar 

  5. Alker, D., Campbell, S.F., Cross, P.E., Burgess, R.A., Carter, A.J., and Gardiner, D.G., J. Med. Chem., 1989, vol. 32, pp. 2381–2388.

    Article  PubMed  CAS  Google Scholar 

  6. Alker, D., Burges, R.A., Campbell, S.F., Carter, A.J., Cross, P.E., Gordiner, D.G., Humphrey, M.J., and Stopher, D.A., J. Chem. Soc., Perkin Trans., 1992, vol. 2, p. 1137.

    Google Scholar 

  7. Arrowsmith, J.E., Campbell, S.F., Cross, P.E., Burges, R.A., and Gardiner, D.G., J. Med. Chem., 1989, vol. 32, pp. 562–568.

    Article  PubMed  CAS  Google Scholar 

  8. Arrowsmith, J.E., Campbell, S.F., Cross, P.E., Stubbs, J.K., Burges, R.A., Gardiner, D.G., and Blackburn, R.A., J. Med. Chem., 1986, vol. 26, pp. 1696–1702.

    Article  Google Scholar 

  9. Liang, J.C., Yeh, J.L., Wang, C.S., Liou, S.F., and Tsai, C.H., Chen, I., J. Bioorg. Med. Chem., 2002, vol. 10, pp. 719–730.

    Article  CAS  Google Scholar 

  10. Caron, G., Ermondi, G., Damiano, A., Navaroli, L., Tsinman, O.K., Ruell, J.A., and Avdeef, A., Bioorg. Med. Chem., 2004, vol. 12, pp. 6107–6118.

    Article  PubMed  CAS  Google Scholar 

  11. Mahlotra, H.S. and Plosker, G.L., Drugs, 2001, vol. 61, pp. 989–996.

    Article  Google Scholar 

  12. Hilgeroth, A., Mini-Rev. Med. Chem., 2002, vol. 2, pp. 235–245.

    Article  PubMed  CAS  Google Scholar 

  13. Hilgeroth, A. and Lilie, H., Eur. J. Med. Chem., 2003, vol. 38, pp. 495–499.

    Article  PubMed  CAS  Google Scholar 

  14. Avendano, C. and Menendez, J.C., Curr. Med. Chem., 2002, vol. 9, pp. 159–193.

    Article  PubMed  CAS  Google Scholar 

  15. Avendano, C. and Menendez, J.C., Med. Chem. Rev. Online, 2004, vol. 1, pp. 419–444.

    Article  CAS  Google Scholar 

  16. Boumendjel, A., Baubichon-Cortary, H., Trompier, D., Perrotton, T., and Die Pietro, A., Med. Res. Rev., 2005, vol. 25, pp. 453–472.

    Article  PubMed  CAS  Google Scholar 

  17. Donkor, I.O., Zhou, X., Schmidt, J., Agrawal, K.C., and Kishore, V., Bioorg. Med. Chem., 1998, vol. 6, pp. 563–568.

    Article  PubMed  CAS  Google Scholar 

  18. Atwal, K.S., Swanson, B.N., Unger, S.E., Floyd, D.M., Mereland, S., Hedberg, A.B., and O’Reilly, C., J. Med. Chem., 1991, vol. 34, pp. 806–811.

    Article  PubMed  CAS  Google Scholar 

  19. Atwal, K.S., Rovnyak, G.C., Kimball, S.D., Floyd, D.M., Mereland, S., Swanson, B.N., Gougoutas, D.Z., Schwartz, J., Smilie, K.M., and Malley, M.F., J. Med. Chem., 1990, vol. 33, pp. 2629–2635.

    Article  PubMed  CAS  Google Scholar 

  20. Paraskar, A.S. and Sudalai, A., Indian J. Chem., 2007, vol. 46B, pp. 331–335.

    CAS  Google Scholar 

  21. Cui, C.B., Kakeya, H., Okada, G., Onose, R., and Osada, H., J. Antibiot., 1996, vol. 49, pp. 527–533.

    Article  PubMed  CAS  Google Scholar 

  22. Tsuda, M., Mugishima, T., Komatzu, K., Sone, T., Tanaka, M., Mikami, Y., Shiro, M., Ohizumii, Y., and Kobayashi, J., Tetrahedron Lett., 2003, vol. 59, pp. 3227–3230.

    Article  CAS  Google Scholar 

  23. Zhang, X. and Smith, C.D., Mol. Pharmacol., 1996, vol. 49, pp. 288–294.

    PubMed  CAS  Google Scholar 

  24. Efange, S.M.N., Kamath, A.P., Khare, A.B., Kung, M.P., Mach, R.H., and Parsons, S.M., J. Med. Chem., 1997, vol. 40, pp. 3905–3914.

    Article  PubMed  CAS  Google Scholar 

  25. Goehring, R.R., Org. Prep. Proced. Int., 1995, vol. 27, pp. 691–694.

    Article  CAS  Google Scholar 

  26. Edmondson, S., Danishefsky, S.J., Lorenzino, L.S., and Rosen, N., J. Am. Chem. Soc., 1999, vol. 121, pp. 2147–2155.

    Article  CAS  Google Scholar 

  27. Palucki, B.L., Feighner, S.D., Pong, S.S., McKee, K.K., Hrenick, D.L., Tan, C., Howard, A.D., Van der Ploeg, L.H., Patchett, A.A., and Nargund, R.P., Bioorg. Med. Chem. Lett., 2001, vol. 11, P. 1955.

    Article  Google Scholar 

  28. Harrell, C.M., Vyas, K.P., Zhang, K.P., Zhang, K., Gilbert, J., Pettibone, D.J., Patane, M.A., Bock, M.G., Freidinger, R.M., and Cluchowski, C., J. Med. Chem., 1999, vol. 42, pp. 4778–4793.

    Article  PubMed  Google Scholar 

  29. Efange, S.M., Kamath, A.P., Khare, A.B., Kung, M.P., Mach, R.H., and Parsons, S.M., J. Med. Chem., 1997, vol. 40, p. 3905.

    Article  PubMed  CAS  Google Scholar 

  30. Charmbers, M.S., Baker, R., Billington, D.C., Knight, A.K., Middlemiss, D.N., and Wong, E.H., J. Med. Chem., 1995, vol. 35, pp. 2033–2039.

    Article  Google Scholar 

  31. Bednarek, M.A., Feighner, S.D., Pong, S.S., McKee, K.K., Hreniuk, D.L., Silva, M.V., Warren, V.A., Howard, A.D., Van der Ploeg, L.H., and Heck, J.V., J. Med. Chem., 2000, vol. 43, pp. 4370–4376.

    Article  PubMed  CAS  Google Scholar 

  32. Nargund, R.P., Sebhat, I.Ye.Z., Barakat, K., Weinberg, D., MacNeil, T., Kalyani, R., Martin, W., Cashen, D., Chen, H., Drisko, J., Mosley, R., Fong, T., Stearns, R., Miller, R., Tamvakopoulos, R., Colwell, L., Strack, A., Shen, X., Tan, C., Pong, S.S., Howard, A., Sailer, A., Hickey, G., MacIntyre, E., Van der Ploeg, L., and Patchett, A., in Abstracts of Papers, 222nd ACS National Meeting, Chicago, IL, US, August 2001.

  33. Bondensgaard, K., Ankersen, M., Thogersen, H., Hansen, B.S., Wulff, B.S., and Bywater, R.P., J. Med. Chem., 2004, vol. 47, pp. 888–899.

    Article  PubMed  CAS  Google Scholar 

  34. Patchett, A.A., J. Med. Chem., 2002, vol. 45, pp. 5609–5616.

    Article  PubMed  CAS  Google Scholar 

  35. Dandia, A., Sarawgi, P., Bingham, A.L., Drake, J.E., and Hursthouse, M.B., J. Chem. Res., 2007, pp. 155–159.

    Google Scholar 

  36. Dandia, A., Singh, R., Khaturia, S., Merienne, C., Morgant, A., Loupy, A., Bioorg. Med. Chem. Lett., 2006, vol. 14, pp. 2409–2417.

    Article  CAS  Google Scholar 

  37. Gould, J.C. and Bowie, J.H., Edinburgh Med. J., 1952, vol. 59, pp. 178–199.

    CAS  Google Scholar 

  38. Provine, H. and Hadley, S., J. Clin Microbiol., 2000, vol. 38, pp. 537–541.

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Gajanand Sharma.

Additional information

The article is published in the original.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sharma, G., Sharma, R., Sharma, M. et al. Synthesis and synergistic, additive inhibitory effects of novel spiro derivatives against ringworm infections. Russ J Bioorg Chem 39, 318–328 (2013). https://doi.org/10.1134/S106816201303014X

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S106816201303014X

Keywords

Navigation