Skip to main content
SpringerLink
Log in

Microwave-assisted synthesis and antimicrobial evaluation of novel pyrazolines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A series of 6-(5-aryl-4,5-dihydro-1H-pyrazol-3-yl)-2,2-dimethylchroman-7-ol and 6-(5-aryl-4,5-dihydro-1H-pyrazol-3-yl)-2,2-dimethylchroman-5-ol derivatives have been synthesized from the corresponding chalcones and hydrazine hydrate in the presence of sodium acetate under microwave irradiation involving the Michael addition followed by cycloaddition. All the newly synthesized 18 compounds were screened for their in vitro antimicrobial activity. Most of the compounds displayed very good to excellent antimicrobial activity in comparison to standard drugs streptomycin and nystatin.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Figure 1

Similar content being viewed by others

References

  1. Williams, D. A.; Lemke, T. L. Foye's Principles of Medicinal Chemistry; 5th ed.; Lippincott Williams and Wilkins, 2002, p. 275.

  2. Gold, H. S.; Moellering, R. C. N. Engl. J. Med. 1996, 335, 1445.

    Article  CAS  Google Scholar 

  3. Cohen, M. L. Science 1992, 257, 1050.

    Article  CAS  Google Scholar 

  4. Abdel-Wahab, B. F.; Abdel-Aziz, H. A.; Ahmed, E. M. Eur. J. Med. Chem. 2009, 44, 2632.

    Article  CAS  Google Scholar 

  5. Nauduri, D.; Reddy, G. B. Chem. Pharm. Bull. 1998, 46, 1254.

    Article  CAS  Google Scholar 

  6. Abid, M.; Azam, A. Bioorg. Med. Chem. Lett. 2006, 16, 2812.

    Article  CAS  Google Scholar 

  7. Prasad, Y. R.; Rao, A. L.; Prasoona, L.; Murali, L. K.; Kumar, P. R. Bioorg. Med. Chem. Lett. 2005, 15, 5030.

    Article  CAS  Google Scholar 

  8. Ozdemir, Z.; Kandilci, H. B.; Gumusel, B.; Calis, U.; Bilgin, A. A. Eur. J. Med. Chem. 2007, 42, 373.

    Article  Google Scholar 

  9. Rathish, I. G.; Javed, K.; Ahmad, S.; Bano, S.; Alam, M. S.; Pillai, K. K.; Singh, S.; Bagchi, V. Bioorg. Med. Chem. Lett. 2009, 19, 255.

    Article  CAS  Google Scholar 

  10. Taylor, E. C.; Patel, H. H. Tetrahedron 1992, 48, 8089.

    Article  CAS  Google Scholar 

  11. Lange, J. H.; Coolen, H. K.; Van Stuivenberg, H. H.; Dijksman, J. A.; Herremans, A. H.; Ronken, E.; Keizer, H. G.; Tipker, K. J. Med. Chem. 2004, 47, 627.

    Article  CAS  Google Scholar 

  12. Valenti, P.; Bisi, A.; Rampa, A.; Belluti, F.; Gobbi, S.; Zampiron, A.; Carrara, M. Bioorg. Med. Chem. 2000, 8, 239.

    Article  CAS  Google Scholar 

  13. Larget, R.; Lockhart, B.; Renard, P.; Largeron, M. A. Bioorg. Med. Chem. Lett. 2000, 10, 835.

    Article  CAS  Google Scholar 

  14. Groweiss, A.; Cardellins, J. H.; Boyd, M. R. J. Nat. Prod. 2000, 63, 1537.

    Article  CAS  Google Scholar 

  15. Khan, I. A.; Avery, M. A.; Burandt, C. L.; Goins, D. K.; Mikell, J. R.; Nash, T. E.; Azadega, A.; Walker, L. A. J. Nat. Prod. 2000, 63, 1414.

    Article  CAS  Google Scholar 

  16. Pietta, P. J. J. Nat. Prod. 2000, 63, 1035.

    Article  CAS  Google Scholar 

  17. Ray, S.; Grover, P. K.; Kamboj, V. P.; Setty, B. S.; Kar, A. B.; Anand, N. J. Med. Chem. 1976, 19, 276.

    Article  CAS  Google Scholar 

  18. Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.

    Article  CAS  Google Scholar 

  19. Vishnuvardhan Reddy, K.; Sampath Rao, P.; Ashok, D. Synth. Commun. 1999, 29, 2365.

    Article  Google Scholar 

  20. Rajani, P.; Ashok, D.; Sharma, P. N. J. Indian Chem. Soc. 1990, 67, 854.

    CAS  Google Scholar 

  21. Ashok, D.; Hanumatha Rao, V.; Srinivas, P. Heterocycl. Commun. 2013, 19, 363.

    Article  CAS  Google Scholar 

  22. Ashok, D.; Mohan Gandhi, D.; Vikas Kumar, A.; Srinivas, G. Med. Chem. Res. 2014, 23, 3005.

    Article  CAS  Google Scholar 

  23. Kalena, G. P.; Jain, A.; Banerji, A. Molecules 1997, 2, 100.

    Article  CAS  Google Scholar 

  24. Murthy, Y. L. N.; Surya Prabha, R.; Seetharam, S. Indian J. Chem. 2004, 43B, 361.

    CAS  Google Scholar 

  25. Meth-Cohn, O.; Narine, B.; Tarnowski, B. A. J. Chem. Soc., Perkin Trans. 1 1981, 1520.

  26. Amir, M.; Kumar, S. Indian J. Chem. 2005, 44B, 2532.

    CAS  Google Scholar 

  27. Aggarwal, R.; Kumar, V.; Singh, S. P. Indian J. Chem. 2007, 46B, 1332.

    CAS  Google Scholar 

  28. Ozdemir, A.; Turan-Zitouni, G.; Kaplancikh, Z. A.; Revial, G.; Guven, K. Eur. J. Med. Chem. 2008, 42, 403.

    Article  Google Scholar 

  29. Revol-Junelles, A. M.; Mathis, R.; Krier, F.; Delfour, A.; Lefebvre, G. Lett. Appl. Microbiol. 1996, 23, 120.

    Article  CAS  Google Scholar 

  30. Narender, T.; Papi Reddy, K. Tetrahedron Lett. 2007, 48, 7628.

    Article  CAS  Google Scholar 

  31. Barry, A. L.; Coyle, M. B.; Thornsberry, C.; Gerlach, E. H.; Hawkinson, R. W. J. Clin. Microbiol. 1979, 10, 885.

    CAS  Google Scholar 

Download references

We thank the Head of Department of Chemistry, Osmania University, Hyderabad, for providing laboratory facilities. One of the authors (MGD) is grateful to University Grants Commission, New Delhi, for the award of Senior Research Fellowship. We also thank the CFRD analytical team, Osmania University, for providing spectral analysis facilities.

Author information

Authors and Affiliations

  1. Department of Chemistry, Osmania University, Tamaka, Hyderabad, 500 007, India

    Ashok Dongamanti, Mohan Gandhi Devulapally, Vikas Kumar Aamate & Srinivas Gundu

Authors
  1. Ashok Dongamanti
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mohan Gandhi Devulapally
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Vikas Kumar Aamate
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Srinivas Gundu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ashok Dongamanti.

Additional information

Supporting material to this article containing of 1H NMR, 13C NMR, and mass spectra of the synthesized compounds is available online at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(10), 872–882

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supporting material

(PDF 5911 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dongamanti, A., Devulapally, M.G., Aamate, V.K. et al. Microwave-assisted synthesis and antimicrobial evaluation of novel pyrazolines. Chem Heterocycl Comp 51, 872–882 (2015). https://doi.org/10.1007/s10593-015-1790-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1790-6

Keywords

Search

Navigation