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POM theoretical calculations and experimental verification of the antibacterial potential of 5-hydroxy-4-(substituted-amino)-2(5H)-furanones

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Abstract

The structure and antibacterial activity of previously synthesized and tested compounds 4-amino-5-hydroxy 2(5H)-furanones 2a–h have been investigated. These compounds have previously been screened against Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922, and Pseudomonas aeruginosa ATCC 27853. Here we report results from POM analysis of their interaction with bacterial targets. The structure and governing force of the antibacterial pharmacophore site of furanones 2a–h were established on the basis of a hypothetical and semi-empirical antibacterial (Xδ+–Yδ−) pharmacophore site.

Graphical abstract

From structure–activity relationship studies, it seems that the functionalized moiety (HO-C-C-NH-R) of the five membered furanone ring and the supplementary halogen substituent are essential for the anti-bacterial activity of this series.

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Notes

  1. Osiris molecular properties calculation software is available online at the site: www.osiris.com.

References

  1. J. Coombs, E. Lattmann, H.M.R. Hoffmann, Synthesis 9, 1367 (1998)

    Article  Google Scholar 

  2. P. Pantazis, Leuk. Res. 19, 775 (1995)

    Article  CAS  Google Scholar 

  3. Q. Cai, J.R. Lindsey, R. Zhang, Int. J. Oncol. 10, 953 (1997)

    CAS  Google Scholar 

  4. E. Lattmann, S. Dunn, S. Niamsanit, N. Sattayasai, Bioorg. Med. Chem. Lett. 15, 919 (2005)

    Article  CAS  Google Scholar 

  5. J. Gasteiger, Empirical Methods for the Calculation of Physicochemical Data of Organic Compounds, in: Physical Property Prediction in Organic Chemistry, Ed. C. Jochum, M. G. Hicks, J. Sunkel, (Springer, Heidelberg, 1988) p. 119

  6. T.B. Hadda, B. Rahima, A. Kerbal, B.F. Baba, M. Akkurt, G. Demailly, M. Benazza, Arkivoc ii, 1 (2008)

    Google Scholar 

  7. T.B. Hadda, R. Badri, A. Kerbal, B.F. Baba, M. Akkurt, G. Demailly, M. Benazza, Arkivoc xiv, 276 (2007)

    Article  Google Scholar 

  8. G.A. Houari, A. Kerbal, B. Bennani, M.F. Baba, M. Daoudi, T.B. Hadda, Arkivoc xii, 42 (2008)

    Article  Google Scholar 

  9. T.B. Hadda, M. Akkurt, M.F. Baba, M. Daoudi, B. Bennani, A. Kerbal, Z.H. Chohan, J. Enz. Inhib. Med. Chem. 24, 457 (2009)

    Article  Google Scholar 

  10. A. Parvez, M. Jyotsna, M.H. Youssoufi, T.B. Hadda, Phosphorus, Sulfur Silicon Related Elem. 185, 1500 (2010)

    Article  CAS  Google Scholar 

  11. A. Jarrahpour, M. Motamedifar, M. Zarei, M.H. Youssoufi, M. Mimouni, Z.H. Chohan, T.B. Hadda, Phosphorus, Sulfur Silicon Related Elem. 185, 491 (2010)

    Article  CAS  Google Scholar 

  12. Z.H. Chohan, M.H. Youssoufi, A. Jarrahpour, T.B. Hadda, Eur. J. Med. Chem. 45, 1189 (2010)

    Article  CAS  Google Scholar 

  13. Z.H. Chohan, S.H. Sumrra, M.H. Youssoufi, T.B. Hadda, Eur. J. Med. Chem. 45, 2739 (2010)

    Article  CAS  Google Scholar 

  14. A. Parvez, V. Tiwari, J. Sheikh, R. Dongre, M.H. Youssoufi, T.B. Hadda, Eur. J. Med. Chem. 45, 4370 (2010)

    Article  CAS  Google Scholar 

  15. A. Parvez, J. Meshram, M.H. Youssoufi, T.B. Hadda, Phosphorus, Sulfur Silicon Related Elem. 17, 1500 (2010)

    Article  Google Scholar 

  16. Z.H. Chohan, H.A. Shad, L. Toupet, T.B. Hadda, M. Akkurt, J. Chem. Crystallogr. (2010). doi:10.1007/s10870-010-9856-x

  17. Z.H. Chohan, S.H. Sumrra, M.H. Youssoufi, T.B. Hadda, J. Coord. Chem. 63, 3981 (2010)

    Article  CAS  Google Scholar 

  18. A. Parvez, J. Meshram, J. Sheikh, V. Tiwari, R. Dongre, T.B. Hadda, Eur. J. Med. Chem. 45, 4370 (2010)

    Article  CAS  Google Scholar 

  19. R.D. Jawarkar, V.H. Masand, K.N. Patil, D.T. Mahajan, M.H. Youssoufi, T.B. Hadda, S.L. Kumbhare, Der Pharm. Chem. 2, 875 (2010)

    Google Scholar 

  20. B. Bennani, A. Kerbal, M. Daoudi, B.F. Baba, G.A. Houari, A. Jalbout, M. Mimouni, M. Benazza, G. Demailly, M. Akkurt, S.Ö. Yýldýrým, T.B. Hadda, Arkivoc xvi, 19 (2007)

    Article  Google Scholar 

  21. P. Ertl, B. Rohde, P. Selzer, J. Med. Chem. 43, 3714 (2000)

    Article  CAS  Google Scholar 

  22. D.E. Clark, J. Pharm. Sci. 88, 807 (1999)

    Article  CAS  Google Scholar 

  23. C.W. Chang, R.F. Spanjersberg, M.W. Beukers, A.P. IJzerman, J. Med. Chem. 47, 6529 (2004)

    Article  CAS  Google Scholar 

  24. V.N. Viswanadhan, A.K. Ghose, G.R. Revankar, R.K. Robins, J. Chem. Inf. Comput. 29, 163 (1989)

    Article  CAS  Google Scholar 

  25. C.A. Lipinski, F. Lombardo, B.W. Dominy, P.J. Feeney, Adv. Drug Deliv. Rev. 46, 3 (2001)

    Article  CAS  Google Scholar 

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Acknowledgments

Professor Taibi Ben Hadda is indebted to the Celeron Company, Switzerland, for help with POM analysis.

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Authors and Affiliations

  1. Laboratoire Chimie Matériaux, Faculté Sciences, Université Med Premier, Oujda, Morocco

    Taibi B. Hadda

  2. Laboratoire de Chimie Physique des Biomolécules et Interfaces Biologiques, Faculté des Sciences de la Nature et de la Vie, Université de Mascara, 29000, Mascara, Algérie

    Teffaha Fergoug

  3. Department of Chemistry, Science College, King Saud University, P.O. Box 2455, Riyadh, 11451, Saudi Arabia

    Ismail Warad

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  1. Taibi B. Hadda
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  2. Teffaha Fergoug
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  3. Ismail Warad
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Correspondence to Taibi B. Hadda.

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Hadda, T.B., Fergoug, T. & Warad, I. POM theoretical calculations and experimental verification of the antibacterial potential of 5-hydroxy-4-(substituted-amino)-2(5H)-furanones. Res Chem Intermed 39, 1963–1971 (2013). https://doi.org/10.1007/s11164-012-0729-0

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