Skip to main content
SpringerLink
Log in

Synthesis and antimicrobial activity of 2H-pyrimido[2,1-b]benzothiazol-2-ones

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

4-Phenyl-2H-pyrimido[2,1-b]benzothiazol-2-ones have been synthesized in quantitative yields by the reaction of 2-aminobenzothiazoles with alkynoic acid. The antimicrobial activity of the synthesized compounds was tested against bacterial species, Bacillus coagulans, Bacillus subtilis, Staphylococcus aureus, and Pseudomonas aeruginosa. The synthesized compounds have shown significant activity against microorganisms which can be correlated with the fused heterocyclic systems.

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

Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. R.R. Gupta, M. Kumar, V. Gupta, Heterocyclic Chemistry, vol. I (Springer, Berlin, 1998)

    Google Scholar 

  2. R.R. Gupta, M. Kumar, V. Gupta, Heterocyclic Chemistry, vol. II (Springer, Berlin, 1999)

    Google Scholar 

  3. F. Palagiano, L. Arenare, P. De Caprariis, G. Grandolini, V. Ambrogi, L. Perioli, W. Filippelli, G. Falcone, F. Rossi, Farmaco 51, 483 (1996)

    CAS  Google Scholar 

  4. P.J. Roy, K. Landry, Y. Leblanc, Heterocycles 45, 2239 (1997)

    Article  CAS  Google Scholar 

  5. C.O. Kappe, Tetrahedron 49, 6937 (1993)

    Article  CAS  Google Scholar 

  6. A. Dandia, S. Khaturia, P. Sarawgi, A. Jain, Phosphorous Sulphur Silicon Relat. Elem. 182, 2529–2539 (2007)

    Article  CAS  Google Scholar 

  7. R.S. Varma, Green Chem. 1, 43 (1999)

    Article  CAS  Google Scholar 

  8. K.S. Atwal, B.N. Swanson, S.E. Unger, J. Med. Chem. 34, 806 (1991)

    Article  CAS  Google Scholar 

  9. C.G. Rovnyak, K.S. Atwal, A. Hedberg, J. Med. Chem. 35, 3254 (1992)

    Article  CAS  Google Scholar 

  10. H. Cho, M. Ueda, K. Shima, J. Med. Chem. 32, 2399 (1989)

    Article  CAS  Google Scholar 

  11. F. Russo, G. Romeo, A. Caruso, V. Cutuli, D. Amore, Eur. J. Med. Chem. 29(7–8), 569–578 (1994)

    Article  CAS  Google Scholar 

  12. M.M.M. Gineinah, Sci. Pharm. 69(1), 53–61 (2001)

    CAS  Google Scholar 

  13. R. Arpana, N. Siddiqui, S.A. Khan, Indian J. Pharm. Sci. 69, 10–17 (2007)

    Article  Google Scholar 

  14. C. Landreau, D. Deniaud, M. Evain, A. Reliquet, J.C. Meslin, J. Chem. Soc. Perkin Trans. 1, 741 (2002)

    Article  Google Scholar 

  15. J. Wang, X. Ai, H. Wahe, Z.T. Fomum, O. Sterner, M. Nielsen, M.R. Witt, Pharmacology 60, 175–178 (2000)

    Article  Google Scholar 

  16. G. Trapani, M. Franco, A. Latrofa, A. Carotti, G. Genchi, M. Serra, G. Biggio, M. Liso, Eur. J. Med. Chem. 31, 575–587 (1996)

    Article  CAS  Google Scholar 

  17. A.K. Fogla, V. Ankodia, P.K. Sharma, M. Kumar, Res. Chem. Intermed. 35, 35–41 (2009)

    Article  CAS  Google Scholar 

  18. V. Ankodia, P.K. Sharma, V. Gupta, M. Kumar, Heterocycl. Commun. 14, 3–155 (2008)

    Google Scholar 

  19. B.S. Rathore, M. Kumar, Bioorg. Med. Chem. 14, 5678 (2006)

    Article  CAS  Google Scholar 

  20. R.R. Gupta, M. Kumar, Synthesis, Reactions and Properties of Phenothiazines. in “Phenothiazines and 1,4-Benzothiazines” (Chemical and Biomedical Aspects), ed. by R.R. Gupta (Elsevier, Amsterdam, 1988), pp. 1–161

    Google Scholar 

  21. K.G. Baheti, S.B. Kapratwar, S.V. Kuberkar, Synth. Commun. 32(14), 2237–2243 (2002)

    Article  CAS  Google Scholar 

  22. A. Shaabani, A. Rahmati, S. Naderi, Bioorg. Med. Chem. Lett. 15, 5553–5557 (2005)

    Article  CAS  Google Scholar 

  23. M.S. Pingle, S.P. Vartale, V.N. Bhosale, S.V. Kuberkar, Arkivoc x, 190–198 (2006)

  24. A.R. Katritzky, J.W. Rogers, R.M. Witek, S.K. Nair, Arkivoc viii, 52–60 (2004)

  25. C.K. Chan, J.C.N. Ma, T.C.W. Mak, J. Chem. Soc. Perkin Trans. 2, 1070 (1977)

    Google Scholar 

  26. P.F. Asobo, H. Wahe, J.T. Mbafor, A.E. Nkengfack, Z.T. Fomum, E.F. Sopbue, D. Doepp, J. Chem. Soc. Perkin Trans. 1, 457 (2001)

    Article  Google Scholar 

  27. B.S. Rathore, M. Kumar, Heteroatom Chem. 18, 81–86 (2007)

    Article  CAS  Google Scholar 

  28. B.S. Rathore, M. Kumar, Res. Chem. Intermed. 32(7), 647 (2006)

    Article  CAS  Google Scholar 

  29. A.D. Jordan, C. Luo, A.B. Reitz, J. Org. Chem. 68, 8693 (2003)

    Article  CAS  Google Scholar 

  30. C.H. Collins, Microbiological Methods (Butterworths, London, 1967), p. 364

    Google Scholar 

  31. K.R. Cruickshank, Medical Microbiology, A Guide to Diagnosis and Control of Infection, 2nd edn. (E.S. Livingston Ltd., Edinburgh and London, 1968)

Download references

Acknowledgments

The authors are thankful to the head of the Department of Chemistry, University of Rajasthan, Jaipur (India) for providing the necessary laboratory as well as instrumentation facilities (IR, 1HNMR and 13C NMR). The director of the RSIC, CDRI, Lucknow (India) is acknowledged for providing mass spectrometry of the synthesized compound. We express our thanks to UGC, New Delhi, for providing Meritorious student fellowship to P.K.S.

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Rajasthan, Jaipur, 302055, India

    Praveen Kumar Sharma & M. Kumar

  2. Mahatma Gandhi Institute of Applied Science, JECRC Campus, Jaipur, India

    Vimal Mohan

Authors
  1. Praveen Kumar Sharma
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Vimal Mohan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Praveen Kumar Sharma.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sharma, P.K., Kumar, M. & Mohan, V. Synthesis and antimicrobial activity of 2H-pyrimido[2,1-b]benzothiazol-2-ones. Res Chem Intermed 36, 985–993 (2010). https://doi.org/10.1007/s11164-010-0211-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-010-0211-9

Keywords

Search

Navigation