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Journal of the Iranian Chemical Society

, Volume 16, Issue 3, pp 465–477 | Cite as

Synthesis of new triazole tethered derivatives of curcumin and their antibacterial and antifungal properties

  • Maryam Esmaeelzadeh
  • Peyman SalehiEmail author
  • Morteza Bararjanian
  • Sajjad Gharaghani
Original Paper
  • 46 Downloads

Abstract

New derivatives of curcumin connected to 1,2,3-triazole ring were synthesized by Knoevenagel reaction of the middle carbon with aromatic aldehydes, followed by alkyne-azide 1,3-dipolar cycloaddition. These new compounds were evaluated for their antimicrobial activity against Staphylococcus aureus, Escherichia coli, Bacillus cereus and Pseudomonas aeruginosa. Many of the synthesized compounds showed a better antibacterial and antifungal activity in comparison with the parent molecule, curcumin. Then quantitative structure–activity relationship (QSAR) modeling was performed to determine the structural descriptors which correlate to the antibacterial and antifungal activities with the synthesized curcumin derivatives. QSAR study showed a good agreement between the experimental results and the predicted values.

Keywords

Antimicrobial activities Click chemistry Curcumin Natural lead compound Knoevenagel QSAR 

Notes

Acknowledgements

Financial support by Shahid Beheshti University Research Council is gratefully acknowledged.

References

  1. 1.
    A. Goel, A.B. Kunnumakkara, B.B. Aggarwal, Biochem. Pharmacol. 75, 787 (2008)CrossRefGoogle Scholar
  2. 2.
    L. Fang, S. Gou, X. Liu, F. Cao, L. Cheng, Bioorg. Med. Chem. Lett. 24, 40 (2014)CrossRefGoogle Scholar
  3. 3.
    M. Gordaliza, Clin. Transl. Oncol. 9, 767 (2008)CrossRefGoogle Scholar
  4. 4.
    I. Ali, A. Haque, K. Saleem, M.F. Hsieh, Bioorg. Med. Chem. 21, 3808 (2013)CrossRefGoogle Scholar
  5. 5.
    R. Sharma, aJ. Gescher, W.P. Steward, Eur. J. Cancer 41, 1955 (2005)CrossRefGoogle Scholar
  6. 6.
    F. Payton, P. Sandusky, W.L. Alworth, J. Nat. Prod. 70, 143 (2007)CrossRefGoogle Scholar
  7. 7.
    A. Minassi, G. Sánchez-Duffhues, J.A. Collado, E. Muñoz, G. Appendino, J. Nat. Prod. 76, 1105 (2013)CrossRefGoogle Scholar
  8. 8.
    X. Wei, Z.-Y. Du, X. Zheng, X.-X. Cui, A.H. Conney, K. Zhang, Eur. J. Med. Chem. 53, 235 (2012)CrossRefGoogle Scholar
  9. 9.
    A.P. Zambre, V.M. Kulkarni, S. Padhye, S.K. Sandur, B.B. Aggarwal, Bioorg. Med. Chem. 14, 7196 (2006)CrossRefGoogle Scholar
  10. 10.
    K. Priyadarsini, Molecules 19, 20091 (2014)CrossRefGoogle Scholar
  11. 11.
    V. Lampe, J. Milobedzka, Ber. Der Dtsch. Chem. Ges. 46, 2235 (1913)CrossRefGoogle Scholar
  12. 12.
    A. Yousefi, R. Yousefi, F. Panahi, S. Sarikhani, A. Zolghadr, A. Bahaoddini, A. Khalafi-nezhad, Int. J. Biol. Macromol. 78, 46–55 (2015)CrossRefGoogle Scholar
  13. 13.
    F. Zhang, Y.-X. Wang, F.-L. Yang, H.-Y. Zhang, Y.-F. Zhao, Synth. Commun. 41, 347 (2011)CrossRefGoogle Scholar
  14. 14.
    P.K. Sahu, P.K. Sahu, S.K. Gupta, D. Thavaselvam, D.D. Agarwal, Eur. J. Med. Chem. 54, 366 (2012)CrossRefGoogle Scholar
  15. 15.
    N.S. Jha, S. Mishra, S.K. Jha, A. Surolia, Electrochim. Acta 151, 574 (2015)CrossRefGoogle Scholar
  16. 16.
    I. Ali, K. Saleem, D. Wesselinova, A. Haque, Med. Chem. Res. 22, 1386 (2013)CrossRefGoogle Scholar
  17. 17.
    S. Mishra, K. Karmodiya, N. Surolia, A. Surolia, Bioorganic Med. Chem. 16, 2894 (2008)CrossRefGoogle Scholar
  18. 18.
    S. Zorofchian Moghadamtousi, H. Abdul Kadir, P. Hassandarvish, H. Tajik, S. Abubakar, K. Zandi, Biomed Res. Int. 2014, 1 (2014)Google Scholar
  19. 19.
    P. Tyagi, M. Singh, H. Kumari, A. Kumari, K. Mukhopadhyay, PLoS One 10, 1 (2015)Google Scholar
  20. 20.
    L.-M. Li, J. Li, X.-Y. Zhang, Electron. J. Biotechnol. 19, 8 (2016)CrossRefGoogle Scholar
  21. 21.
    J.R. Manjunatha, B.K. Bettadaiah, P.S. Negi, P. Srinivas, Food Chem. 136, 650 (2013)CrossRefGoogle Scholar
  22. 22.
    J. Lal, S.K. Gupta, D. Thavaselvam, D.D. Agarwal, Bioorg. Med. Chem. Lett. 22, 2872 (2012)CrossRefGoogle Scholar
  23. 23.
    Y. Liu, W. Yan, Y. Chen, J.L. Petersen, X. Shi, C.E. Bennett, W. Virginia, V. Uni, Org. Lett. 10, 5389 (2008)CrossRefGoogle Scholar
  24. 24.
    B. Alcaide, P. Almendros, C. Aragoncillo, R. Callejo, M.P. Ruiz, M.R. Torres, J. Org. Chem. 77, 6917 (2012)CrossRefGoogle Scholar
  25. 25.
    N. Pokhodylo, O. Shyyka, V. Matiychuk, Sci. Pharm. 81, 663 (2013)CrossRefGoogle Scholar
  26. 26.
    A. Srivastava, L. Aggarwal, N. Jain, ACS Comb. Sci. 17, 39 (2015)CrossRefGoogle Scholar
  27. 27.
    N.S. Vatmurge, B.G. Hazra, V.S. Pore, F. Shirazi, P.S. Chavan, M.V. Deshpande, Bioorg. Med. Chem. Lett. 18, 2043 (2008)CrossRefGoogle Scholar
  28. 28.
    M. Whiting, J. Muldoon, Y.-C. Lin, S.M. Silverman, W. Lindstrom, A.J. Olson, H.C. Kolb, M.G. Finn, K.B. Sharpless, J.H. Elder, V.V. Fokin, Angew. Chem. Int. Ed. 45, 1435 (2006)CrossRefGoogle Scholar
  29. 29.
    E. De Clercq, Arkivoc 152 (2010)Google Scholar
  30. 30.
    P. Sambasiva Rao, C. Kurumurthy, B. Veeraswamy, G. Santhosh Kumar, Y. Poornachandra, C. Ganesh Kumar, S.B. Vasamsetti, S. Kotamraju, B. Narsaiah, Eur. J. Med. Chem. 80, 184 (2014)CrossRefGoogle Scholar
  31. 31.
    P. Sambasiva Rao, C. Kurumurthy, B. Veeraswamy, G. Santhosh Kumar, P. Shanthan Rao, R. Pamanji, J. Venkateswara Rao, B. Narsaiah, Bioorg. Med. Chem. Lett. 23, 1225 (2013)CrossRefGoogle Scholar
  32. 32.
    G.C. Tron, ?T. Pirali, R.A. Billington, P.L. Canonico, G. Sorba, Med. Res. Rev. 28, 278 (2008)CrossRefGoogle Scholar
  33. 33.
    H.C. Kolb, M.G. Finn, K.B. Sharpless, Angew. Chemie Int. Ed. 40, 2004 (2001)CrossRefGoogle Scholar
  34. 34.
    Z.G. Luo, Y. Zhao, F. Xu, C. Ma, X.M. Xu, X.M. Zhang, Chin. Chem. Lett. 25, 1346 (2014)CrossRefGoogle Scholar
  35. 35.
    V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, Angew. Chem. Int. Ed. Engl. 41, 2596 (2002)CrossRefGoogle Scholar
  36. 36.
    B. Schulze, U.S. Schubert, Chem. Soc. Rev. 43, 2522 (2014)CrossRefGoogle Scholar
  37. 37.
    M. Mohebbi, P. Salehi, M. Bararjanian, A. Aliahmadi, R. Safavi-Sohi, J.B. Ghasemi, Med. Chem. Res. 23, 4531 (2014)CrossRefGoogle Scholar
  38. 38.
    P. Khaligh, P. Salehi, M. Bararjanian, A. Aliahmadi, H.R. Khavasi, S. Nejad-ebrahimi, Chem. Pharm. Bull. 64, 1589 (2016)CrossRefGoogle Scholar
  39. 39.
    P. Salehi, K. Babanezhad-Harikandei, M. Bararjanian, A. Al-Harrasi, M.-A. Esmaeili, A. Aliahmadi, Med. Chem. Res. 25, 1895 (2016)CrossRefGoogle Scholar
  40. 40.
    V.S.P.R. Lingam, R. Vinodkumar, K. Mukkanti, A. Thomas, B. Gopalan, Tetrahedron Lett. 49, 4260 (2008)CrossRefGoogle Scholar
  41. 41.
    S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem. Int. Ed. Engl. 44, 5188 (2005)CrossRefGoogle Scholar
  42. 42.
    P.D. Lister, D.J. Wolter, N.D. Hanson, Clin. Microbiol. Rev. 22, 582 (2009)CrossRefGoogle Scholar
  43. 43.
    J.H. Jorgensen, J.D. Turnidge, Manual of Clinical Microbiology, 9th edn. (American Society for Microbiology, Washington DC, 2007)Google Scholar
  44. 44.
    HyperChem 7.0, Molecular Modeling System. (Hyper Cube Inc, Gainesville, FL, USA, 1993)Google Scholar
  45. 45.
    C.W. Yap, J. Comput. Chem. 32, 1466 (2011)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  • Maryam Esmaeelzadeh
    • 1
  • Peyman Salehi
    • 1
    Email author
  • Morteza Bararjanian
    • 1
  • Sajjad Gharaghani
    • 2
  1. 1.Department of Phytochemistry, Medicinal Plants and Drugs Research InstituteShahid Beheshti UniversityTehranIran
  2. 2.Institute of Biochemistry and Biophysics (IBB)University of TehranTehranIran

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