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Design, Synthesis, Characterization and IN VITRO Antimicrobial and Anthelmintic Evaluation of Metronidazole Derivatives Modified at Position 1

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Pharmaceutical Chemistry Journal Aims and scope

The primary aim of this study was to incorporate biologically active pharmacophores like 1,3,4-thiadiazole and Schiff base moiety into metronidazole without modifying the nitro group. The synergy arising from the successful incorporation of imidazole ring, thiadiazole ring and Schiff’s base pharmacophore was exploited in this research. It was expected that, since these pharmacophores have individual antibacterial and anthelmintic activity, their successful incorporation in one molecule would improve the antibacterial and anthelmintic activity of the compound along with improved safety and efficacy. Some compounds (1, 1b, 1f and 1e) showed significant antibacterial activity compared to the standard. Similarly, compounds 1, 1b and 1g exhibited significant anthelmintic activity against P. excavatus and P. species.

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References

  1. Y. J. Ahn, M. Kwon, J. K. Yoo, et al., J. Econ. Entomol., 86, 1334 – 1338 (1993).

    Article  CAS  Google Scholar 

  2. S. El-Zemity,M. E. Badawy,M. M. Khattab, et al., Int. J. Agric. Biol., 661 – 665 (2006).

  3. A. H. Ceruelos, L. C. Romero-Quezada, J. C. Ruvalcaba Ledezma, et al., Eur. Rev. Med. Pharmacol. Sci., 23, 397 – 401 (2019).

    Google Scholar 

  4. C. Congiu, M. T. Cocco and V. Onnis, Bioorg. Med. Chem. Lett., 18, 989 – 993(2008).

    Article  CAS  Google Scholar 

  5. L. Yurttaş, M. Ertaş, G. A. Çiftçi, et al., Acta Pharm. Sci., 55, 39 – 47(2017).

  6. Y. I. Lin, P. J. Peterson, Y. Yang, et al., Bioorg. Med. Chem. Lett., 16, 1890 – 1902(2008).

    Article  Google Scholar 

  7. T. Nakamura, H. Kakinuma, H. Umemiya, et al., Bioorg. Med. Chem. Lett., 14, 333 – 336 (2004).

    Article  CAS  Google Scholar 

  8. G. Roman, J. G. Riley, J. Z. Vlahakis, et al. Bioorg. Med. Chem., 15, 3225 – 3234 (2007).

    Article  CAS  Google Scholar 

  9. M. A Babizhayev, Life Sci., 78, 2343 – 2357 (2006).

    Article  CAS  Google Scholar 

  10. P. G. Nantermet, J. C. Barrow, et al., Bioorg. Med. Chem. Lett., 14, 2141 – 2145 (2004).

    Article  CAS  Google Scholar 

  11. A. Husain, S. Drabu, N. Kumar, et al., J. Pharm. Bioallied Sci., 5, 154 – 161 (2013).

    Article  Google Scholar 

  12. Q. Li, Q. Hu, X. Wang, et al., Chem. Biol. Drug. Des., 86, 509 – 516 (2015).

    Article  CAS  Google Scholar 

  13. D. Sharma, B. Narasimhan, P. Kumar, et al., Eur. J. Med. Chem., 44, 2347 – 2353 (2009).

    Article  CAS  Google Scholar 

  14. Y. L. Fan, X. H. Jin, Z. P. Huang, et al., Eur. J. Med. Chem., 150, 347 – 365 (2018).

    Article  CAS  Google Scholar 

  15. M. Adib, F. Peytam, R. Shourgeshty, et al., Bioorg. Med. Chem. Lett., 29, 713 – 718 (2019).

    Article  CAS  Google Scholar 

  16. S. Kondaparla, A. Manhas, V. R. Dola, et al., Bioorg. Chem., 80, 204 – 211 (2018).

    Article  CAS  Google Scholar 

  17. S. Ganguly, V. V. Vithlani1, A. K. Kesharwani, et al., Acta Pharm., 61, 187 – 201 (2011).

  18. A. Husain, S. Drabu and N. Kumar, Acta Polon. Pharm. Drug Res., 66, 243 – 248 (2009).

  19. V. R. Mallemula, N. N. Sanghai, V. Himabindu, et al., Res. Chem. Intermed., 41, 2125 – 2138 (2013).

    Article  Google Scholar 

  20. S. D. Bhinge, V. Chature and L. V. Sonawane, Pharm. Chem. J., 49, 367 – 372 (2015).

    Article  CAS  Google Scholar 

  21. G. Naganagowda and B. Padmashali, Phosphorus, Phosphorus Sulfur Silicon Relat. Elem., 185, 1691 – 1700 (2010).

  22. K. N. Venugopala and B. S. Jayashree, Ind. J. Het. Chem., 12, 307 – 310 (2003).

    CAS  Google Scholar 

  23. M. M. Varshney, A. Husain, and V. Parcha, Med. Chem. Res., 23, 4034 – 4041 (2014).

    Article  CAS  Google Scholar 

  24. A. Husaina, M. M. Varshneyb and V. Parchad, Lett. Drug Des. Discov., 15, 103 – 111 (2018).

    Article  Google Scholar 

  25. P. N. Balaji, D. Ranganayakulu and G. V. S. Reddy, Asian J. Pharm. Pharmacol., 3, 9 – 15 (2017).

    CAS  Google Scholar 

  26. R. Rao, K. R. Reddy and K. N. Mahendra, Bulg. Chem. Commun., 46, 11 – 17 (2014).

    CAS  Google Scholar 

  27. S. Baluja, and S. Chanda, Rev. Colomb. Cienc. Quím. Farm., 45, 201 – 218 (2016).

    Article  CAS  Google Scholar 

  28. A. Hussain, K. S. Al-Bayati, N. Rezki, et al., Molecules, 10, 1153 – 1160 (2005).

    Article  Google Scholar 

  29. K. Padhy, V. L. Nag and C. S. Panda, Ind. J. Chem., 38B, 998 – 1001 (1999).

    CAS  Google Scholar 

  30. R. Cruickshank, J. P. Duguid, B. P. Marion, and R. H. A. Swain, in: Medicinal Microbiology, 12th ed. Churchill Livingstone: London (1975), Vol. 2. pp. 196 – 202.

  31. A. Husain, M. V. Munendra, V. Parcha, et al., Bangladesh J. Pharmacol., 10, 555 – 561 (2015).

    Google Scholar 

  32. K. Sahoo, R. Sharma and P. Pattanayak, Med. Chem. Res., 19, 127 – 135 (2010).

    Article  CAS  Google Scholar 

  33. R. Dahiya and D. Pathak, Eur. J. Med. Chem., 42, 772 – 798 (2007).

    Article  CAS  Google Scholar 

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Acknowledgements

The authors are thankful to SAIF, Punjab University and Dr. Ganesh P. Mishra, KSCP, Swami Vivekananda Subharti University, Meerut, for providing and interpreting spectral data.

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Authors and Affiliations

  1. Bhagwant University, Sikar Road, Ajmer, Rajasthan, 305004, India

    Priyabrata Pattanayak & Saravanan Kaliyaperumal

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  1. Priyabrata Pattanayak
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  2. Saravanan Kaliyaperumal
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Correspondence to Priyabrata Pattanayak.

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Pattanayak, P., Kaliyaperumal, S. Design, Synthesis, Characterization and IN VITRO Antimicrobial and Anthelmintic Evaluation of Metronidazole Derivatives Modified at Position 1. Pharm Chem J 56, 191–196 (2022). https://doi.org/10.1007/s11094-022-02620-3

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  • DOI: https://doi.org/10.1007/s11094-022-02620-3

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