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Synthesis and characterization of novel benzothiazole amide derivatives and screening as possible antimitotic and antimicrobial agents

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Abstract

A new series of benzothiazole amide derivatives (9a–l) were synthesized and characterized by Fourier-transform infrared (FT-IR), mass, and 1H and 13C nuclear magnetic resonance (NMR) spectroscopic techniques. The antimitotic activity of the newly synthesized compounds was determined by the Allium assay method, from which mitotic index values were calculated. Here, 9g (14.0 %) and 9l (14.5 %) showed mitotic index values most comparable to that of standard drug (14.4 %), while the remaining compounds showed lower mitotic index values; hence, these compounds inhibit the regular cell division process and are the most promising antimitotic agents. Based on the structural activity relationship, the maximum percentage inhibition was observed for compounds containing electron-withdrawing group, revealing enhanced antimitotic activity, while compounds with electron-donating groups such as furan (9g) and methyl (9l) were comparable to standard. The newly synthesized compounds were also screened for antimicrobial activity, with some of them showing remarkable activity.

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References

  1. K. Kavya, P. Pattanaik, Int. J. Med. Nanotechnol. 1(2), 73 (2014)

    Google Scholar 

  2. J. Fu, K. Cheng, Z. Zhang, R. Fang, H. Zhu, Eur. J. Med. Chem. 45, 2638 (2010)

    Article  CAS  Google Scholar 

  3. A. Gaspar, E.M. Garrido, M. Esteves, E. Quezada, N. Milhazes, J. Garrido, F. Borges, Eur. J. Med. Chem. 44, 2092 (2009)

    Article  CAS  Google Scholar 

  4. D. Ledmicer, L.A. Mitschen, The Organic Drug Synthesis, vol. 2 (Wiley, New York, 1980), p. 248

    Google Scholar 

  5. J.N. Delegado, W.A. Remers, Wilson and Gisvold’s Textbook of Organic Medicinal and Pharmaceutical Chemistry (Lippincott–Raven, Philadelphia, 2004)

    Google Scholar 

  6. A.K. Ghose, V.N. Viswanadhan, J.J. Wendoloski, J. Comb. Chem. 1(1), 55 (1999)

    Article  CAS  Google Scholar 

  7. E.Y. Song, N. Kaur, M.-Y. Park, Y. Jin, K. Lee, G. Kim, K.Y. Lee, J.S. Yang, J.H. Shin, K.-Y. Nam, K.T. No, G. Han, Eur. J. Med. Chem. 43, 1519 (2008)

    Article  CAS  Google Scholar 

  8. S. Kini, S. Swain, A. Gandhi, Indian J. Pharm. Sci. 69(1), 46 (2007)

    Article  CAS  Google Scholar 

  9. M. Bhat, S.L. Belagali, Res. Chem. Intermed. 42(7), 6195 (2016)

    Article  CAS  Google Scholar 

  10. M. Bhat, S.L. Belagali, Int. J. Curr. Eng. Technol. 4(4), 2711 (2014)

    Google Scholar 

  11. M. Bhat, S.L. Belagali, P.S. Rajesh, V. Ravishankar Rai, Monatsh. Chem. (2016). doi:10.1007/s00706-016-1700-3

    Google Scholar 

  12. W.F. Grant, Environ. Health Perspect. 27, 37 (1978)

    Article  CAS  Google Scholar 

  13. B. Umesha, Y.B. Basavaraju, C. Mahendra, S.B. Shivakumar, P.K. Rao, M.H. Krishna, Indo Am. J. Pharm. Res. 4(01), 905 (2014)

    Google Scholar 

  14. M.K. Raj, C. Balachandran, V. Duraipandiyan, P. Agastian, S. Ignacimuthu, A. Vijayakumar, Med. Chem. Res. 22(8), 3823 (2013)

    Article  Google Scholar 

  15. J.R. Dunetz, Y. Xiang, A.R. Baldwin, Org. Lett. 13, 5048 (2011)

    Article  CAS  Google Scholar 

  16. S. Petit, C. Fruit, L. Bischoff, Org. Lett. 12, 4928 (2010)

    Article  CAS  Google Scholar 

  17. M. Thoss, R.W. Seidel, M. Feigel, Tetrahedron 66, 8503 (2010)

    Article  CAS  Google Scholar 

  18. C. Frochot, B. Di Stasio, R. Vanderesse, M.J. Belgy, M. Dodeller, F. Guillemin, M.L. Viriot, B.H. Muriel, Bioorg. Chem. 35, 205 (2007)

    Article  CAS  Google Scholar 

  19. P.G.M. Wuts, T.W. Green, Green’s Protective Groups in Organic Synthesis, 4th edn. (Wiley, New York, 2007)

    Google Scholar 

  20. A. McKillop, A. Hendrson, S.P. Ray, A. Carmen, G.M. Encarnacion, Tetrahedron Lett. 23(33), 3357 (1982)

    Article  CAS  Google Scholar 

  21. E. Campaigne, J.E. Van Verth, J. Org. Chem. 23, 1344 (1958)

    Article  CAS  Google Scholar 

  22. W.E. Valeur, M. Bradley, Chem. Soc. Rev. 38, 606 (2009)

    Article  CAS  Google Scholar 

  23. G. Fissceja, Hereditas 102, 99 (1985)

    Google Scholar 

  24. A. Levan, Heriditas 24, 471 (1938)

    Article  Google Scholar 

  25. K. Rekha, S.N. Kak, A. Langer, Indian J. For. 27, 355 (2004)

    Google Scholar 

  26. W.F. Grant, Environ. Health Perspect. 27, 37 (1978)

    Article  CAS  Google Scholar 

  27. M.D. Makut, S.D. Gyar, G.R.I. Pennap, P. Anthony, Afr. J. Biotechnol. 7, 1216 (2008)

    Google Scholar 

Download references

Acknowledgments

The first author would like to thank the Department of Science and Technology, New Delhi, India, for providing an INSPIRE fellowship (Mahesh Bhat—IF130464) and the Institute of Excellence, University of Mysore, for providing NMR facilities.

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Authors and Affiliations

  1. Environmental Chemistry Laboratory, Department of Studies in Environmental Science, University of Mysore, Manasagangothri, Mysore, 570 006, India

    Mahesh Bhat & S. L. Belagali

  2. Department of Studies in Botany, University of Mysore, Manasagangothri, Mysore, 570 006, India

    N. K. Hemanth Kumar & S. Mahadeva Kumar

Authors
  1. Mahesh Bhat
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  2. S. L. Belagali
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  3. N. K. Hemanth Kumar
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  4. S. Mahadeva Kumar
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Correspondence to Mahesh Bhat.

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Bhat, M., Belagali, S.L., Hemanth Kumar, N.K. et al. Synthesis and characterization of novel benzothiazole amide derivatives and screening as possible antimitotic and antimicrobial agents. Res Chem Intermed 43, 361–378 (2017). https://doi.org/10.1007/s11164-016-2627-3

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