Skip to main content
SpringerLink
Log in

Synthesis, characterization, and antimicrobial activity of novel (E)-1-(aryl)-3-{3, 5-dimethoxy-4-[(1-(aryl)-1H-1,2,3-triazol-4-yl)methoxy]phenyl}prop-2-en-1-ones

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

Abstract

The new chalcone derivatives containing the 1,2,3-triazole ring system, namely, (E)-1-(aryl)-3-{3,5-dimethoxy-4-[(1-(aryl)-1H-1,2,3-triazol-4-yl)methoxy]phenyl}prop-2-en-1-ones, were synthesized in 65–88% yield by the “click chemistry” reactions of substituted acetophenones, 4-hydroxy-3,5-dimethoxy-benzaldehyde, and different substituted azides. The structure of the compounds was determined by the FT-IR, 1H NMR, 13C NMR, and mass spectroscopic analyses. Compounds 6a–6l were screened for in vitro antimicrobial activity by the agar disc diffusion method.

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

Similar content being viewed by others

References

  1. Reichwald, C., Shimony, O., Sacerdoti, S.N., Jaffe, C.L., and Kunick, C., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 1985. DOI: 10.1016/jbmcl.2008.01.112.

    Article  CAS  Google Scholar 

  2. Kumar, R., Mohanakrishnan, D., Sharma, A., Kaushik, N.K., Kalia, K., Sinha, A.K., and Sahal, D., Eur. J. Med. Chem., 2010, vol. 45, p. 5292. DOI: 10.1016/jejmech.2010.08.049.

    Article  CAS  Google Scholar 

  3. Karaman, I., Gezegen, H., Guerdere, M.B., Dingil, A., and Ceylan, M., Chem. Biodiver., 2010, vol. 7, p. 400.

    Article  CAS  Google Scholar 

  4. Dao, T.T., Nguyen, P.H., Lee, H.S., Kim, E., Park, J., Lim, S.I., and Oh, W.K., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 294. DOI: 10.1016/jbmcl.2010.11.016.

    Article  CAS  Google Scholar 

  5. Prasad, Y., Rajendra Rao, A., and Srinivasa Rambabu, R., Asian J. Chem., 2009, vol. 21, p. 907.

    CAS  Google Scholar 

  6. Guzy, J., Vaskova, K.J., Rozmer, Z., Fodor, K., Marekova, M., Poskrobova, M., and Perjesi, P., FEBS Lett., 2010, vol. 584, p. 567. DOI: 10.18052/wwwscipresscom/ILCPA.63.83.

    Article  CAS  Google Scholar 

  7. Bandgar, B.P., Gawande, S.S., Bodade, R.G., Tote, J.V., and Khobragade, C.N., Bioorg. Med. Chem., 2010, vol. 18, p. 1364. DOI: 10.1016/jbmc.2009.11.066.

    Article  CAS  Google Scholar 

  8. Saeed, A., Zachary, O.B., Hasan, A., Melissa, G.L., and Alejandro, C.U., Bioorg. Med. Chem., 2011, vol. 19, p. 2055. DOI: 10.1016/jbmc.2011.01.048.

    Article  Google Scholar 

  9. Bandgar, B.P., Gawande, S.S., Bodade, R.G., Gawande, N.M., and Khobragade, C.N., Bioorg. Med. Chem., 2009, vol. 17, p. 8168. DOI: 10.1016/jbmc.2009.10.035.

    Article  CAS  Google Scholar 

  10. Go, M.L., Wu, X., and Liu, X.L., Curr. Med. Chem., 2005, vol. 12, p. 483.

    Article  CAS  Google Scholar 

  11. Aponte, J.C., Verastegui, M., Malaga, E., Zimic, M., Quiliano, M., and Vaisberg, A.J., Gilman, R.H., and Hammond, G.B., J. Med. Chem., 2008, vol. 51, p. 6230. DOI: 10.1021/jm800812k.

    Article  CAS  Google Scholar 

  12. Shah, A., Khan, A., Qureshi, R., Ansari, F., Nazar, M., and Shah, S., Int. J. Mol. Sci., 2008, vol. 9, p. 1424. DOI: 10.3390/ijms9081424.

    Article  CAS  Google Scholar 

  13. Quintin, J., Desrivot, J., There, S., Mines, P.L., Cresteil, T., and Lewin, G., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 167. DOI: 10.1016/jbmcl.2008.10.126.

    Article  CAS  Google Scholar 

  14. Alvarez, R., Velazquez, S., San, F., Aquaro, S., De, C., Perno, C.F., Karlsson, A., Balzarini, J., and Camarasa, M.J., J. Med. Chem., 1994, vol. 37, p. 4185. DOI: 10.1021/jm00050a015.

    Article  CAS  Google Scholar 

  15. Buckle, D.R., Rockell, C.J.M., Smith, H., and Spicer, B.A., J. Med. Chem., 1986, vol. 29, p. 2262. DOI: 10.1021/jm00161a022.

    Article  CAS  Google Scholar 

  16. Vicentini, C.B., Brandolini, V., Guarneri, M., and Giori, P., Farmaco, 1992, vol. 47, p. 1021

    CAS  Google Scholar 

  17. Fung-Tomc, J., Huczko, E., Minassian, B., and Bonner, D.P., Antimicrob. Agents CH, 1998, vol. 42, p. 313.

    CAS  Google Scholar 

  18. Palhagen S., Canger, R., Henriksen O., van Parys, J.A., Riviere, M.E., and Karolchyk, M. A., Epilepsy Res., 2001, vol. 43, p. 115.

    Article  CAS  Google Scholar 

  19. Genin, M.J., Allwine, D.A., Anderson, D.J, Barbachyn, M.R., Emmert, D.E, Garmon, S.A., Graber, D.R., Grega, K.C., Hester, J.B., Hutchinson, D.K., Morris, J., Reischer, R.J., Ford, C.W., Zurenko, G.E., Hamel, J.C., Schaadt, R.D., Stapert, D., and Yagi, B.H., J. Med. Chem., 2000, vol. 43, p. 953.

    Article  CAS  Google Scholar 

  20. Bourne, Y., Kolb, H.C., Radic, Z., Sharpless, K.B., Taylor, P., and Marchot, P., P. Natl. Acad. Sci. U. S. A., 2004, vol. 101, p. 1449. DOI: 10.1073/pnas.0308206100.

    Article  CAS  Google Scholar 

  21. Willis, R.J. and Marlow, I.D, Eur. Pat. Appl. 400842, 1990 (CA 1991, 114, 164247b).

    Google Scholar 

  22. Morgan, N.H. (CHOMERICS) Eur. Pat. Appl., EP 437979A2 19910724, 1991.

  23. Shin, J.A., Lim, Y.G., and Lee, K.H., J. Org.Chem., 2012, vol. 77, p. 4117. DOI: 10.1021/jo3000095.

    Article  CAS  Google Scholar 

  24. Chittepu, P., Sirivolu, V.R., and Seela, F., Bioorg. Med. Chem., 2008, vol. 16, p. 8427. DOI: 10.1016/jbmc.2008.08.026.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University College of Technology, Osmania University, Hyderabad, 500007, India

    N. J. P. Subhashini, Ch. Sravanthi & K. Sravanthi

  2. Department of Chemistry, University College of Science, Osmania University, Hyderabad, 500007, India

    Shivaraj

Authors
  1. N. J. P. Subhashini
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ch. Sravanthi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. Sravanthi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Shivaraj
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. J. P. Subhashini.

Additional information

The text was submitted by the authors in English.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Subhashini, N.J.P., Sravanthi, C., Sravanthi, K. et al. Synthesis, characterization, and antimicrobial activity of novel (E)-1-(aryl)-3-{3, 5-dimethoxy-4-[(1-(aryl)-1H-1,2,3-triazol-4-yl)methoxy]phenyl}prop-2-en-1-ones. Russ J Gen Chem 86, 1405–1411 (2016). https://doi.org/10.1134/S107036321606027X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107036321606027X

Keywords

Search

Navigation