Skip to main content
SpringerLink
Log in

Synthesis and antimicrobial activity of structurally flexible heterocycles with the 1,4-thiazine heterosystem

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

Abstract

In this work, 4H-1,4-benzothiazines were synthesized by an efficient synthetic method in a single step involving heterocyclization of substituted 2-aminobenzenethiols with β-ketoester. The structures of the synthesized compounds were confirmed by their analytical and spectral data. The synthesized compounds were evaluated for their antimicrobial activity against bacterial species; E. coli and Bacillus cereus. The synthesized compounds showed significant activity against microorganisms, which can be correlated with the privileged heterocyclic structural scaffolds.

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
Fig. 1

Similar content being viewed by others

References

  1. S.J. Teague, A.M. Davis, P.D. Leeson, T. Oprea, Angew. Chem. Int. Ed. 38, 3743–3748 (1999)

    Article  CAS  Google Scholar 

  2. R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown, T.A. Keating, Acc. Chem. Res. 29, 123–131 (1996)

    Article  CAS  Google Scholar 

  3. A. Aiello, E. Fattorusso, P. Luciano, M. Menna, G. Esposito, T. Iuvone, D. Pala, Eur. J. Org. Chem. 89, 8–900 (2003)

    Google Scholar 

  4. Y.-T. Ma, M.-C. Huang, F.-L. Hsu, H.-F. Chang, Phytochemistry 48, 1083–1085 (1998)

    Article  CAS  Google Scholar 

  5. A.A. Mahmoud, A.A. Ahmed, O. Spring, Nat. Prod. Res. 19, 585–589 (2005)

    Article  CAS  Google Scholar 

  6. R.J. Stoodley, A.R. Katritzky (eds.) Advances in heterocyclic chemistry, vol 24 (Academic, New York, 1979) pp. 293–361

  7. M.J. Cook, A.J. Boulton (eds.) Comprehensive heterocyclic chemistry, vol 3 (Pergamon: Oxford 1984) pp. 1037–1038

  8. M.O. Lozinskii, A.F. Karev, G.V. (eds.) vol 2 (JBS Press: Moscow, 2003)

  9. B.C. Galarreta, R. Sifuentes, A.K. Carrillo, L. Sanchez, Bioorg. Med. Chem. 16(14), 6689–6695 (2008)

    Article  CAS  Google Scholar 

  10. Y. Nakamura, Y. Kanda, S. Kunii, N. Motohashi, H. Sakagami, Anticancer 28(2), 1069–1078 (2008)

    Google Scholar 

  11. B. Morak-Mlodawska, K. Pluta, Heterocycles 71(6), 1347–1361 (2007)

    Article  CAS  Google Scholar 

  12. S. Kamila, B. Koh, H. Zhang, E.R. Biehl, Arkivoc 2, 1–14 (2006)

    Google Scholar 

  13. G. Jagath Reddy, K. Srinivasa Rao, Heterocycl. Commun. 11(2), 195–198 (2005)

    Article  Google Scholar 

  14. F. Corelli, F. Manetti, A. Tafi, G. Campiani, V. Nacci, M. Botta, J. Med. Chem. 40, 125–131 (1997)

    Article  CAS  Google Scholar 

  15. M. Bakavoli, H. Sadeghian, Z. Tabatabaei, E. Rezaei, M. Rahimizadeh, M. Nikpour, J. Mol. Mod. 14(6), 471–478 (2008)

    Article  CAS  Google Scholar 

  16. R. Fringuelli, L. Milanese, F. Schiaffella, Rev. Med. Chem. 5(12), 1061–1073 (2005)

    Article  CAS  Google Scholar 

  17. N. Bhavani, S. Perumal, R. Banureka, Acta Cristallographica 59(9), 1400–1402 (2003)

    Article  Google Scholar 

  18. V. Cecchetti, V. Calderone, O. Tabarrini, S. Sabatini, E. Filipponi, L. Testai, R. Spogli, E. Martinotti, A. Fravolini, J. Med. Chem. 46(17), 3670–3679 (2003)

    Article  CAS  Google Scholar 

  19. S. Sabatini, G.W. Kaatz, G.M. Rossolini, D. Brandini, J. Med. Chem. 51(14), 4321–4330 (2008)

    Article  CAS  Google Scholar 

  20. A. Barazarte, J. Camacho, Bioorg. Med. Chem. 16(7), 3661–3674 (2008)

    Article  CAS  Google Scholar 

  21. A.H. Mandour, E.R. El-Sawy, M.S. Ebid, J. Chem. 50(4), 555–568 (2007)

    CAS  Google Scholar 

  22. R.R. Gupta, M. Kumar, Phenothiazines and 1,4-benzothiazines: chemical and biomedical aspects (Elsevier: Amsterdam 1988) pp. 1–161

  23. R.R. Gupta, K.G. Ojha, Phenothiazines and 1, 4-benzothiazines: chemical and biomedical aspects (Elsevier, Amsterdam, 1988), pp. 163–269

    Google Scholar 

  24. B.K. Sharma, P.K. Sharma, M. Kumar, Synth. Commun. 40(16), 2347–2352 (2010)

    Article  CAS  Google Scholar 

  25. V. Ankodia, P.K. Sharma, M. Kumar, Hetrocycl. Commun. 15(2), 127–133 (2009)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  27. V. Ankodia, P.K. Sharma, V. Gupta, M. Kumar, Hetrocycl. Commun. 14(3), 155 (2008)

    Article  CAS  Google Scholar 

  28. M. Kumar, N. Sharma, R. Gupta, R.R. Gupta, Heterocycl. Commun. 4, 187 (1998)

    Article  CAS  Google Scholar 

  29. P.K. Sharma, V. Mohan, M. Kumar, Res. Chem. Intermed. 36, 985–993 (2010)

    Article  CAS  Google Scholar 

  30. B.S. Rathore, M. Kumar, Heteroatom. Chem. 18(1), 81 (2007)

    Article  CAS  Google Scholar 

  31. B.S. Rathore, M. Kumar, Bioorg. Med. Chem. 14, 5678–5682 (2006)

    Article  CAS  Google Scholar 

  32. B.S. Rathore, M. Kumar, Res. Chem. Intermed. 32(7), 647–651 (2006)

    Article  CAS  Google Scholar 

  33. N.B. Ambati, V. Anand, P. Hanumanthu, Synth. Commun. 27, 1487 (1997)

    Article  CAS  Google Scholar 

  34. A.D. Jordan, L. Chi, J. Org. Chem. 68(22), 8693 (2003)

    Article  CAS  Google Scholar 

  35. Y. Maki, M. Suzuki, T. Yamada, Chem. Pharm. Bull. 14(7), 770 (1966)

    CAS  Google Scholar 

  36. F. Duro, P. Condarilli, G. Ronsisvalle, Ann. Chim. 63, 45 (1973)

    CAS  Google Scholar 

  37. F. Duro, P. Condarilli, G. Ronsisvalle, Chem. Abstr. 80, 95856 (1974)

    Google Scholar 

  38. R.R. Gupta, G.S. Kalwania, R. Kumar, Bull. Chem. Soc. Jap. 57(8), 4810 (1984)

    Article  Google Scholar 

  39. S. Kano, Y. Yuasa, T. Ono, S. Shibuya, Heterocycles 12, 681 (1979)

    Article  CAS  Google Scholar 

  40. G. Liso, G. Trabani, V. Berardi, A. Latrofa, J. Heterocycle. Chem. 17, 4–793 (1980)

    Google Scholar 

  41. G. Liso, G. Trabani, V. Berardi, A. Latrofa, Chem. Abstr. 94, 30681 (1981)

    Google Scholar 

  42. A.Y. Chenko, Ukr. Khim. Zh. 35(11), 1185 (1969)

    Google Scholar 

  43. A.Y. Chenko, Chem. Abstr. 72, 56667 (1970)

    Google Scholar 

  44. H. Nagase, Agric. Chem. Pharm. Bull. 22(1), 42 (1974)

    CAS  Google Scholar 

  45. M.R. Islami, F. Mollazehi, A. Badiei, H. Sheibani, Arkivoc xv, 25–29 (2005)

    Google Scholar 

  46. M.R. Islami, F.H. Nassab, H. Sheibani, A. Hassanpour, Arkivoc xv, 175–180 (2006)

    Google Scholar 

  47. M.R. Islami, H. Sheibani, A. Hassanpour, Arkivoc xv, 68–75 (2006)

    Google Scholar 

  48. M.R. Islami, H. Sheibani, A. Hassanpour, K. Saidi, Phosphorus Sulfur 183, 13–20 (2008)

    Google Scholar 

  49. V. Tandon, A.K. Mishra, B.S. Chhikara, Heterocycles 63, 1057 (2004)

    Article  Google Scholar 

  50. W. Zhong, Y. Zhang, Tetrahedron Lett. 42, 3125–3127 (2001)

    Article  CAS  Google Scholar 

  51. H. Hussain, V.U. Ahmad, I.R. Green, K. Krohn, J. Hussain, A. Badshah, Arkivoc (xiv) 289–299 (2007)

  52. A. Rahman, M.I. Choudhary, W.J. Thomsen, Bioassay techniques for drug development (Harwood Academic Publishers, The Netherlands, 2001), p. 16

    Book  Google Scholar 

  53. M.I. Choudhary, W.J. Thomsen, Bioassay techniques for drug development (Harwood Academic Publishers, The Netherlands, 2001), p. 22

    Google Scholar 

  54. M. Serwar, T. Akhtar, S. Hameed, K.M. Khan, ARKIVOC (vii) 210–221 (2009)

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 facilities as well as instrumentation facilities (IR, and 1HNMR). The director of the RSIC, CDRI, Lucknow (India) is acknowledged for providing mass spectra of the synthesized compounds. We express our thanks to UGC, New Delhi, for providing a meritorious student fellowship to one of the authors (P.K.S.).

Author information

Authors and Affiliations

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

    Praveen Kumar Sharma, Ankur Fogla, B. S. Rathore & M. Kumar

Authors
  1. Praveen Kumar Sharma
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ankur Fogla
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. S. Rathore
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. Kumar.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sharma, P.K., Fogla, A., Rathore, B.S. et al. Synthesis and antimicrobial activity of structurally flexible heterocycles with the 1,4-thiazine heterosystem. Res Chem Intermed 37, 1103–1111 (2011). https://doi.org/10.1007/s11164-011-0320-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-011-0320-0

Keywords

Search

Navigation