Pharmaceutical Chemistry Journal

, Volume 50, Issue 3, pp 172–180 | Cite as

Novel Armed Pyrazolobenzothiazine Derivatives: Synthesis, X-Ray Crystal Structure and POM analyses of Biological Activity Against Drug Resistant Clinical Isolate of Staphylococcus aureus

  • Zara Sajid
  • Matloob Ahmad
  • Sana Aslam
  • Usman Ali Ashfaq
  • Ameer Fawad Zahoor
  • Furqan Ahmad Saddique
  • Masood Parvez
  • Abdul Hameed
  • Sadia Sultan
  • Hsaine Zgou
  • Taibi Ben Hadda
Article
First Online:
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Novel structural hybrids of pyrazolobenzothiazine and triazole ring systems have been prepared to observe a synergistic effect of the two ring systems. The methodology involves condensation of pyrazolobenzothiazine rings with methyl chloroacetate, followed by hydrazide formation. The hydrazides were converted to triazoles through the formation of intermediate potassium salts of dithiocarbazate. The final compounds as well as intermediates were screened for their antibacterial activity against a multidrug resistant strain of Staphylococcus aureus. It was interesting to observe that dithiocarbazates (7a, 7b) and target triazoles (8a, 8b) exhibited antibacterial activity.

Keywords

pyrazolobenzothiazine dioxides triazole antibacterial pharmacophore site Petra/Osiris/Molinspiration (POM) analyses 
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Notes

Acknowledgements

One of the authors (M. Ahmad) highly acknowledges “Higher Education Commission of Pakistan” for providing “Startup research grant” No. PM-IPFP/HRD/HEC/2011/382. Professor T. Ben Hadda would like to thank ACTELION, the Biopharmaceutical Company of Swiss, for the calculations of molecular properties.

References

  1. 1.
    N. S. Jayasundara, MSc Thesis, Queensland University of Technology, Brisbane, Australia (2014).Google Scholar
  2. 2.
    L. G. Miller and B. A. Diep, Clin. Infect. Dis., 46, 752 – 760 (2008).CrossRefPubMedGoogle Scholar
  3. 3.
    A. Mastoraki, I. Kriaras, E. Douka, et al., Interact. Cardiovasc. Thor. Surg., 7, 452 – 456 (2008).CrossRefGoogle Scholar
  4. 4.
    M. E. Stryjewski and G. R. Corey, Clin. Infect. Dis., 58, S9 – S10 (2014).CrossRefGoogle Scholar
  5. 5.
    F. Şahin, I. Karaman, M. Güllüce, H. Öðütçü, et al., J. Ethnopharmacol., 87, 61 – 65 (2003).CrossRefPubMedGoogle Scholar
  6. 6.
    G. Ravizzola, G. Pinsi, M. Cesana, et al., Curr. Microbiol., 24, 349 – 353 (1992).CrossRefGoogle Scholar
  7. 7.
    E. H. Abbas and T. Farghaly, Monatsh. Chem., 141, 661 – 667 (2010).CrossRefGoogle Scholar
  8. 8.
    M. Shafiq, M. Zia-Ur-Rehman, I. U. Khan, et al., Chil. Chem. Soc., 56, 527 – 531 (2011).CrossRefGoogle Scholar
  9. 9.
    M. Ahmad, S. U. F. Rizvi, H. L. Siddiqui, et al., Med. Chem. Res., 21, 2340 – 2348 (2012).CrossRefGoogle Scholar
  10. 10.
    P. Sharma and M. Kumar, Res. Chem. Intermed., 1 – 8 (2014).Google Scholar
  11. 11.
    P. Sharma, M. Kumar and S. Vats, Med. Chem. Res., 21, 2072 – 2078 (2012).CrossRefGoogle Scholar
  12. 12.
    M. Bukhari, H. L. Siddiqui, M. Ahmad, et al., Med. Chem. Res., 21, 2885 – 2895 (2012).CrossRefGoogle Scholar
  13. 13.
    M. Ahmad, H. L. Siddiqui, M. Zia-Ur-Rehman, and M. Parvez, Eur. J. Med. Chem., 45, 698 – 704 (2010).CrossRefPubMedGoogle Scholar
  14. 14.
    M. Ahmad, H. L. Siddiqui, J. M. Gardiner, et al., Med. Chem. Res., 22, 794 – 805 (2013).CrossRefGoogle Scholar
  15. 15.
    S. Aslam, M. Ahmad, M. Zia-Ur-Rehman, et al., Arch. Pharm. Res., 37, 1380 – 1393 (2014).CrossRefPubMedGoogle Scholar
  16. 16.
    Z. Otwinowski and W. Minor, in: Methods in Enzymology, Vol. 276: Macromolecular Crystallography. Part A, Ed. by C. W. Carter, Jr. and R. M. Sweet, Academic Press, New York (1997), pp. 307 – 326.Google Scholar
  17. 17.
    R. Hooft, COLLECT: User’s Manual, Nonius B. V., Delft, Netherlands (1998).Google Scholar
  18. 18.
    A. Altomare, M. Cascarano, C. Giacovazzo and A. Guagliardi, J. Appl. Cryst., 26, 343 – 350 (1993).CrossRefGoogle Scholar
  19. 19.
    P. T. Beurskens, G. Admiraal, G. Beurskens, et al., The DIRDIF-94 Program System:Technical Report of the Crystallography Laboratory, University of Nijmegen, Netherlands (1994).Google Scholar
  20. 20.
    G. M. Sheldrick, SHELXL97: A Program for Refinement of Crystal Structures, University of Gottingen, Germany (1997).Google Scholar
  21. 21.
    C. K. Johnson, ORTEPII: Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, USA (1976).Google Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • Zara Sajid
    • 1
  • Matloob Ahmad
    • 1
  • Sana Aslam
    • 2
  • Usman Ali Ashfaq
    • 3
  • Ameer Fawad Zahoor
    • 1
  • Furqan Ahmad Saddique
    • 1
  • Masood Parvez
    • 4
  • Abdul Hameed
    • 5
  • Sadia Sultan
    • 6
  • Hsaine Zgou
    • 7
  • Taibi Ben Hadda
    • 8
  1. 1.Department of ChemistryGovernment College UniversityFaisalabadPakistan
  2. 2.Department of ChemistryGovernment College Women UniversityFaisalabadPakistan
  3. 3.Department of Bioinformatics and BiotechnologyGovernment College UniversityFaisalabadPakistan
  4. 4.Department of ChemistryUniversity of CalgaryAlbertaCanada
  5. 5.HEJ Research Institute of Chemistry, International Center for Chemical and Biological SciencesUniversity of KarachiKarachiPakistan
  6. 6.Faculty of Pharmacy, Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns)Universiti Teknologi MARABandar Puncak AlamMalaysia
  7. 7.Ibn Zohr University, Polydisciplinary FacultyOuarzazateMorocco
  8. 8.Laboratoire Chimie Matériaux, FSOUniversité Mohammed PremierOujdaMorocco

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