Research on Chemical Intermediates

, Volume 40, Issue 4, pp 1715–1725 | Cite as

Synthesis and antimicrobial activity of novel chalcone derivatives

  • Xianwen Fang
  • Bingqin Yang
  • Zhao Cheng
  • Pengfei Zhang
  • Meipan Yang


A series of novel 3-[N, N-bis(2-hydroxyethyl)-amino]-chalcone derivatives 3a–3j were synthesized by the aldol condensation of [N, N-bis(2-hydroethyl)-3-amino]-acetophenone 2 with aromatic aldehydes. Their structures were further confirmed by ESI-HRMS, 1H NMR, IR and elemental analysis. X-ray analysis reveals crystal 3b is a monoclinic system with P21/n space group. The antimicrobial activities of the newly synthesized chalcones in vitro were evaluated and the results indicated that most compounds presented moderate to good antimicrobial activities, especially the antifungal capability. Compounds 3a, 3d, 3f and 3g revealed obvious potency against Candida albicans with MIC values of 32 μg/mL, which were better compared with others.


Chalcone Synthesis Crystal structure Broth tube dilution method Antimicrobial activity 

Supplementary material

11164_2013_1076_MOESM1_ESM.doc (4.8 mb)
Supplementary material 1 (DOC 4923 kb)


  1. 1.
    P.B. Bandgar, S.A. Patil, R.N. Gacche, B.L. Korbad, S.B. Hote, S.N. Kinkar, S.S. Jalde, Bioorg. Med. Chem. Lett. 20, 730 (2010)CrossRefGoogle Scholar
  2. 2.
    L.M. Ni, C.Q. Meng, J.A. Sikorski, Expert Opin. Ther. Pat. 14, 1669 (2004)CrossRefGoogle Scholar
  3. 3.
    X.F. Zhu, B.F. Xie, J.M. Zhou, G.K. Feng, Z.C. Liu, X.Y. Wei, F.X. Zhang, M.F. Liu, Y.X. Zeng, Mol. Pharmacol. 67, 1444 (2005)CrossRefGoogle Scholar
  4. 4.
    S.F. Nielsen, S.B. Christensen, G. Cruciani, A. Kharazmi, T. Liljefors, J. Med. Chem. 41, 4819 (1998)CrossRefGoogle Scholar
  5. 5.
    J.R. Dimmock, N.M. Kandepu, M. Hetherington, J.W. Quail, U. Pugazhenthi, A.M. Sudom, M. Rose, P. Chamankhah, E. Pass, T.M. Allen, S. Halleran, J. Szydlowski, B. Mutus, M. Tannous, E.K. Manavathu, T.G. Myers, E.D. Clercq, J. Balzarini, J. Med. Chem. 41, 1014 (1998)CrossRefGoogle Scholar
  6. 6.
    O. Sabzevari, G. Galati, M.Y. Moridani, A. Siraki, P.J. O’Brien, Chem. Biol. Interact. 148, 57 (2004)CrossRefGoogle Scholar
  7. 7.
    Y.M. Lin, Y. Zhou, M.T. Flavin, L.M. Zhou, W. Niea, F.C. Chen, Bioorg. Med. Chem. 10, 2795 (2002)CrossRefGoogle Scholar
  8. 8.
    M. Liu, P. Wilairat, M.L. Go, J. Med. Chem. 44, 4443 (2001)CrossRefGoogle Scholar
  9. 9.
    B. Madan, S. Batra, B. Ghosh, Mol. Pharmacol. 58, 526 (2000)Google Scholar
  10. 10.
    P.M. Sivakumar, G. Iyer, L. Natesan, M. Doble, Appl. Sur. Sci. 256, 6018 (2010)CrossRefGoogle Scholar
  11. 11.
    P.M. Sivakumar, S. Priya, M. Doble, Chem. Biol. Drug Des. 73, 403 (2009)CrossRefGoogle Scholar
  12. 12.
    J.R. Wingard, H.L. Leather, Oncol. 15, 351 (2001)Google Scholar
  13. 13.
    A.R. Gomes, H. Westh, H. Lencastre, Antimicrob. Agents Chemother. 50, 3237 (2006)CrossRefGoogle Scholar
  14. 14.
    K. Coleman, Drug Discov. Today Ther. Strateg. 1, 455 (2004)CrossRefGoogle Scholar
  15. 15.
    E.A. Palombo, S.J. Semple, J. Ethnopharmacol. 77, 151 (2001)CrossRefGoogle Scholar
  16. 16.
    M.X. Yang, X. Lin, P. Yu, L.J. Chen, S.X. Liu, Chin. J. Chem 23, 1407 (2005)CrossRefGoogle Scholar
  17. 17.
    NCCLS, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically M7-A5, vol. 20 (National Committee on Clinical Laboratory Standards, Wayne, 2000), p. 2Google Scholar
  18. 18.
    Y.K. Qi, B. Jiao, X.D. Ma, W.P. Cui, S.T. Ma, Arch. Pharm. Chem. Life Sci. 8, 458 (2010)CrossRefGoogle Scholar
  19. 19.
    S. Wattanasin, W.S. Murphy, Synthesis 8, 647 (1980)CrossRefGoogle Scholar
  20. 20.
    B.D. Palmer, W.R. Wilson, S.M. Pullen, W.A. Denny, J. Med. Chem. 33, 112 (1990)CrossRefGoogle Scholar
  21. 21.
    G.H. Wu, L. Wang, S.M. Wang, L. Li, X.Y. Xu, J.X. Yang, Chin. J. Syn. Chem. 17, 503 (2009). (in Chinese)Google Scholar
  22. 22.
    E.D. D’silva, G.K. Podagatlapalli, S.V. Rao, D. Narayana, S.M. Dharmaprakash, Cryst. Growth Des. 11, 5362 (2011)CrossRefGoogle Scholar
  23. 23.
    B.K. Sarojini, B. Narayana, B.V. Ashalatha, J. Indira, K.G. Lobo, J. Cryst. Growth 295, 54 (2006)CrossRefGoogle Scholar
  24. 24.
    W.C. Huang, C.H. Lee, J.W. Liu, J. Microbiol. Immunol. Infect. 43, 470 (2010)CrossRefGoogle Scholar
  25. 25.
    P.L. Zhao, C.L. Liu, W Huang, Y.Z. Wang, G.F. Yang, J. Agric. Food Chem. 55, 5697 (2007)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  • Xianwen Fang
    • 1
  • Bingqin Yang
    • 1
  • Zhao Cheng
    • 1
  • Pengfei Zhang
    • 1
  • Meipan Yang
    • 1
  1. 1.Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of EducationCollege of Chemistry & Materials Science, Northwest UniversityXi’anChina

Personalised recommendations