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Synthesis of bioactive substituted pyrazolylbenzothiazinones

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Abstract

Pyrazolylbenzothiazinones have been synthesized in good yields by the reaction of 2-hydrazinocarbonymethyl-3,4-dihydro-2H-1,4-benzothiazin-3-ones with β-diketone in the presence of ethanol. The structures of synthesized pyrazolylbenzothiazinones were confirmed on the basis of their analytical and spectral data. The antimicrobial activities of the synthesized compounds have also been included.

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References

  1. J. Elguero, In Comprehensive Heterocyclic Chemistry, vol. 3, ed. by A.R. Katritzky, C.W. Rees, E.V.F. Scriven (Pergamon Press, London, 1996), pp. 1–75

  2. S. Zhihua, J. Guan, C. Dennis, Bioorg. Med. Chem. Lett. 10, 601–604 (2000)

    Article  Google Scholar 

  3. T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, J. Med. Chem. 40, 1347–1365 (1997)

    Article  CAS  Google Scholar 

  4. R.R. Gupta, Phenothiazines and 1,4-Benzothiazines Chemical and Biomedical Aspects (Elsevier, Amsterdam, 1988), pp. 163–269

    Google Scholar 

  5. K.G. Nazarenko, N.A. Shtil, M.O. Lozinski, Tetrahedron 63, 7723–7727 (2007)

    Article  Google Scholar 

  6. A. Shah, Y. Natipara, D. Sureja, N. Motohashi, Anticancer Res. 18, 3001–3004 (1998)

    CAS  Google Scholar 

  7. R. Fringuelli, F. Schiafella, A. Vecchiarelli, J. Chemother. 13(1), 9–14 (2001)

    Article  CAS  Google Scholar 

  8. S. Barriga, P. Fuertes, T. Torroba, J. Org. Chem. 69, 3672–3682 (2004)

    Article  CAS  Google Scholar 

  9. T. Yamamoto, M. Hori, I. Watanabe, Chem. Pharm. Bull. 48, 843–849 (2000)

    Article  CAS  Google Scholar 

  10. Y. Watanabe, K. Osanai, T. Nishi, Bioorg. Med. Chem. Lett. 6(16), 1923–1926 (1996)

    Article  CAS  Google Scholar 

  11. D. Armesine, G. Trapani, V. Arrivo, J. Heterocycl. Chem. 37, 1611–1616 (2000)

    Article  Google Scholar 

  12. V. Calderone, R. Spogli, A. Martelli, J. Med. Chem. 51(16), 5085–5092 (2008)

    Article  CAS  Google Scholar 

  13. M. Fujita, K. Yamamoto, Y. Kawashima, H. Yamauchi, J. Med. Chem. 33, 1898–1905 (1990)

    Article  CAS  Google Scholar 

  14. S.B. Kale, B.K. Karale, J. Heterocyl. Chem. 44(2), 289–301 (2007)

    Article  CAS  Google Scholar 

  15. S. Sabatini, D. Brandini, A. Fravolini, J. Med. Chem. 51(14), 4321–4330 (2008)

    Article  CAS  Google Scholar 

  16. G. Campiani, A. Garofalo, I. Fiorini, J. Med. Chem. 38, 4393–4410 (1995)

    Article  CAS  Google Scholar 

  17. M.O. Lozinskii, A.M. Demchenko, in Advanced Methods of Synthesis and Modifications of Heterocycles, vol. 2 ed. by V.G. Karcev (JBS, Moscow 2003)

  18. D. Lednicer, L.A. Mitscher, Organic Chemistry of Drugs Synthesis A, vol. 1–3 (Wiley, New York, 1977)

    Google Scholar 

  19. G. Turan-Zitouni, P. Chevallet, Eur. J. Med. Chem. 35, 635–641 (2000)

    Article  CAS  Google Scholar 

  20. R.N. Comber, R.J. Gray, Carbohydr. Res. 216, 441–452 (1991)

    Article  CAS  Google Scholar 

  21. L. Xin-Hua, Bioorg. Med. Chem. 16, 4075–4082 (2008)

    Article  Google Scholar 

  22. Y. Li, J. Liu, J. Agric. Food Chem. 54, 3636–3640 (2006)

    Article  CAS  Google Scholar 

  23. M. Manpadi, S. Rogelj, J. Med. Chem. 50, 5183–5192 (2007)

    Article  Google Scholar 

  24. C.B. Vicentini, S. Guccione, J. Agric. Food Chem. 53, 3848–3855 (2005)

    Article  CAS  Google Scholar 

  25. R.D. Clark, J. Agric. Food Chem. 44, 3643–3652 (1996)

    Article  CAS  Google Scholar 

  26. A. Barazarte, G. Loo, Eur. J. Med. Chem. 44, 1303–1310 (2009)

    Article  CAS  Google Scholar 

  27. E. Akbas, I. Berber, Farmaco 60, 23–26 (2005)

    Article  CAS  Google Scholar 

  28. A.A. Bekhita, T. Abdel-Aziem, Bioorg. Med. Chem. 12, 1935–1945 (2004)

    Article  Google Scholar 

  29. P.K. Sharma, M. Kumar, V. Mohan, Res. Chem. Intermed. 36(8), 985–993 (2010)

  30. S. Vats, P.K. Sharma, M. Kumar, Med. Chem. Res. 21, 2072–2078 (2012)

    Article  Google Scholar 

  31. M. Kumar, P.K. Sharma, Res. Chem. Intermed. 37, 1103–1111 (2011)

    Article  Google Scholar 

  32. S.K. Mukherji, M. Jain, Ind. J. Chem. 33B, 990–991 (1994)

    CAS  Google Scholar 

  33. D.R. Shridhar, B. Ram, Ind. J. Chem. 24 B, 992–994 (1985)

    Google Scholar 

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

    Article  CAS  Google Scholar 

  35. A. Fogla, P.K. Sharma, M. Kumar, Res. Chem. Intermed. 35(1), 35–41 (2009)

    Article  CAS  Google Scholar 

  36. V. Ankodia, P.K. Sharma, M. Kumar, Heterocycl. Commun. 14(3), 155–160 (2008)

    Article  CAS  Google Scholar 

  37. B.K. Sharma, P.K. Sharma, M. Kumar, One-pot. Synth. Commun. 40(16), 2347–2352 (2010)

    Article  CAS  Google Scholar 

  38. T. Aotsuka, H. Hosono, Chem. Pharm. Bull. 42(6), 1264–1271 (1994)

    Article  CAS  Google Scholar 

  39. K.C. Kim, H.S. Kim, J. Korean Chem. Soc. 46(6), 585–589 (2002)

  40. H. Hussain, V.U. Ahmad, Arkivoc xiv, 289–299 (2007)

  41. A. Rahman, W.J. Thomsen, Bioassay Techniques for Drug Development (Harwood Academic Publishers, The Netherlands, 2001), p. 16

    Book  Google Scholar 

  42. M. Serwar, T. Akhtar, Arkivoc vii, 210–221(2009)

  43. M.I. Choudhary, W.J. Thomsen, Bioassay Techniques for Drug Development (Harwood Academic Publishers, The Netherlands, 2001), p. 22

    Google Scholar 

  44. V.V. Dabholkar, R.P. Gavande, Indian J. Chem. 51B(8), 1173–1179 (2012)

    CAS  Google Scholar 

Download references

Acknowledgments

The authors are thankful to the Head, Department of Chemistry, University of Rajasthan, Jaipur (India) for providing necessary laboratory facilities as well as instrumentation facilities (IR, and 1HNMR). The Director RSIC, CDRI, Lucknow (India) is acknowledged for providing mass spectra of the synthesized compounds. We express our thanks to University Grant Commission, New Delhi, for providing meritorious student fellowship to one of us (P.K.S.).

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Authors and Affiliations

  1. Department of Chemistry, Lovely Professional University, Phagwara, 144402, Punjab, India

    Praveen Kumar Sharma

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

    M. Kumar

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  1. Praveen Kumar Sharma
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  2. M. Kumar
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Correspondence to Praveen Kumar Sharma.

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Sharma, P.K., Kumar, M. Synthesis of bioactive substituted pyrazolylbenzothiazinones. Res Chem Intermed 41, 6141–6148 (2015). https://doi.org/10.1007/s11164-014-1727-1

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