Skip to main content
Log in

Convenient Synthesis of Novel Chalcone and Pyrazoline Sulfonamide Derivatives as Potential Antibacterial Agents

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

Abstract

Novel chalcone sulfonamide derivatives were synthesized starting from benzophenones and aldehydes in 3 steps. Also, (E)-3-(4-chlorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one was converted to different pyrazoline in four steps. The synthesis of sulfonamides was carried out under solvent-free conditions at room temperature and the products were obtained in high purity after a simple work-up without using any chromatography method for purification. All of the products were evaluated for their in vitro antibacterial activity against Staphylococcus aureus and Escherichia coli.

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. Nowakowska, Z., Eur. J. Med. Chem., 2007, vol. 42, pp. 125–137.

    Article  CAS  Google Scholar 

  2. Nielsen, S.F., Boesen, T., Larsen, M., Schønning, K., and Kromann, H., Bioorg. Med. Chem., 2004, vol. 12, pp. 3047–3054.

    Article  CAS  Google Scholar 

  3. Lahtchev, K., Batovska, D., Parushev, S., Ubiyvovk, V., and Sibirny, A., Euro. J. Med. Chem., 2008, vol. 43, pp. 2220–2228.

    Article  CAS  Google Scholar 

  4. Yadav, H.L., Gupta, P., Pawar, R., Singour, P., and Patil, U., Med. Chem. Res., 2011, vol. 20, pp. 461–465.

    Article  CAS  Google Scholar 

  5. Domínguez, J.N., León, C., Rodrigues, J., de Domínguez, N.G., Gut, J., and Rosenthal, P. J., Il Farmaco, 2005, vol. 60, pp. 307–311.

    Article  Google Scholar 

  6. Hsieh, C.-T., Hsieh, T.-J., El-Shazly, M., Chuang, D.-W., Tsai, Y.-H., Yen, C.-T., Wu, S.-F., Wu, Y.-C., and Chang, F.-R., Bioorg. Med. Chem. Lett., 2012, vol. 22, pp. 3912–3915.

    Article  CAS  Google Scholar 

  7. Syam, S., Abdelwahab, S.I., Al-Mamary, M. A., and Mohan, S., Molecules, 2012, vol. 17, pp. 6179–6195.

    Article  CAS  Google Scholar 

  8. Al-Refai, M., Ibrahim, M.M., Alsohaili, S., and Geyer, A., Phosphorus Sulfur Silicon Relat. Elem., 2017, vol. 192, pp. 560–564.

    Article  CAS  Google Scholar 

  9. Sharma, P.K., Kumar, S., Kumar, P., Kaushik, P., Sharma, C., Kaushik, D., and Aneja, K. R., Med. Chem. Res., 2012, vol. 21, pp. 2945–2954.

    Article  CAS  Google Scholar 

  10. Samshuddin, S., Narayana, B., Sarojini, B.K., Khan, M.T.H., Yathirajan, H.S., Raj, C.G.D., and Raghavendra, R., Med. Chem. Res., 2012, vol. 21, pp. 2012–2022.

    Article  CAS  Google Scholar 

  11. Lv, P.-C., Li, H.-Q., Sun, J., Zhou, Y., and Zhu, H.-L., Bioorg. Med. Chem., 2010, vol. 18, pp. 4606–4614.

    Article  CAS  Google Scholar 

  12. Rahman, M.A., and Siddiqui, A.A., Int. J. Pharm. Sci. Drug Res., 2010, vol. 2, pp. 165–175.

    CAS  Google Scholar 

  13. Lv, P.-C., Sun, J., Luo, Y., Yang, Y., and Zhu, H.-L., Bioorg. Med. Chem. Lett., 2010, vol. 20, pp. 4657–4660.

    Article  CAS  Google Scholar 

  14. Massah, A.R., Adibi, H., Khodarahmi, R., Abiri, R., Majnooni, M.B., Shahidi, S., Asadi, B., Mehrabi, M., and Zolfigol, M.A., Bioorg. Med. Chem., 2008, vol. 16, pp. 5465–5472.

    Article  CAS  Google Scholar 

  15. El-Din, N.S., Chem. Heterocycl. Comp., 2000, vol. 36, pp. 449–454.

    Article  CAS  Google Scholar 

  16. Ryckebusch, A., Deprez-Poulain, R., Debreu-Fontaine, M.-A., Vandaele, R., Mouray, E., Grellier, P., and Sergheraert, C., Bioorg. Med. Chem. Lett., 2002, vol. 12, pp. 2595–2598.

    Article  CAS  Google Scholar 

  17. Yan, L., Bertarelli, D.C., Hayallah, A.M., Meyer, H., Klotz, K.-N., and Müller, C.E., J. Med. Chem., 2006, vol. 49, pp. 4384–4391.

    Article  CAS  Google Scholar 

  18. Supuran, C.T., Casini, A., and Scozzafava, A., Med. Res. Rev., 2003, vol. 23, pp. 535–558.

    Article  CAS  Google Scholar 

  19. Dinsmore, C J., Williams, T.M., O’Neill, T.J., Liu, D., Rands, E., Culberson, J.C., Lobell, R.B., Koblan, K.S., Kohl, N.E., and Gibbs, J.B., Bioorg. Med. Chem. Lett., 1999, vol. 9, pp. 3301–3306.

    Article  CAS  Google Scholar 

  20. Shoaib Ahmad Shah, S., Rivera, G., and Ashfaq, M., Mini Rev. Med. Chem., 2013, vol. 13, pp. 70–86.

    Article  Google Scholar 

  21. Massah, A.R., Asadi, B., Hoseinpour, M., Molseghi, A., Kalbasi, R.J., and Naghash, H.J., Tetrahedron, 2009, vol. 65, pp. 7696–7705.

    Article  CAS  Google Scholar 

  22. Massah, A., Dabagh, M., Shahidi, S., Naghash, H.J., Momeni, A., and Aliyan, H., J. Iran. Chem. Soc., 2009, vol. 6, pp. 405–411.

    Article  CAS  Google Scholar 

  23. Massah, A.R., Kazemi, F., Azadi, D., Farzaneh, S., Aliyan, H., Naghash, H.J., and Momeni, A., Lett. Org. Chem., 2006, vol. 3, pp. 235–241.

    Article  CAS  Google Scholar 

  24. Sharma, N., Sharma, A., Kumar, R., Shard, A., and Sinha, A.K., Eur. J. Org. Chem., 2010, vol. 2010, pp. 6025–6032.

    Article  Google Scholar 

  25. Sharath, R., Krishna, V., Sathyanarayana, B., and Harish, B., Pharmacologyonline, 2008, vol. 2, pp. 517–528.

    Google Scholar 

Download references

ACKNOWLEDGMENTS

We acknowledge financial support from the Shahreza Branch, Islamic Azad University (IAUSH) Research Council. Also, we thank Professor R. F. W. Jackson (Department of Chemistry, The University of Sheffield UK) for helpful comments on the manuscript and S. Bradshaw (Department of Chemistry, The University of Sheffield UK) for recording NMR spectra.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. R. Massah.

Ethics declarations

COMPLIANCE WITH ETHICAL STANDARDS

The authors declare that they have no conflict of interest. This article does not contain any studies involving animals or human participants performed by any of the authors.

Conflict of Interests

The authors declare that they have no conflicts of interest.

Additional information

Corresponding author: phone: +98–321-3292522; e-mail: Massah@iaush.ac.ir.

Supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bonakdar, A.P., Sadeghi, A., Aghaei, H.R. et al. Convenient Synthesis of Novel Chalcone and Pyrazoline Sulfonamide Derivatives as Potential Antibacterial Agents. Russ J Bioorg Chem 46, 371–381 (2020). https://doi.org/10.1134/S1068162020030048

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162020030048

Keywords:

Navigation