Advertisement

Pharmaceutical Chemistry Journal

, Volume 53, Issue 1, pp 52–56 | Cite as

Synthesis, Characterization and Biological Evaluations of New Imidazo[4,5-a]Acridines as Potential Antibacterial Agents

  • Nasrin Karimi
  • Mehdi PordelEmail author
  • Abolghasem Davoodnia
  • Hamid Sadeghian
  • Mina Mousavian
Article
  • 3 Downloads

The significance of bacterial infections and the early success achieved with some antibiotic drugs have prompted the search for new antibacterial agents. Some new derivatives of 3H-imidazo[4,5-a]acridines are introduced as new powerful antibacterial agents against Gram-positive species. The reaction of N-alkyl-5-nitrobenzimidazoles with arylacetonitriles under basic conditions led to the synthesis of 3H-imidazo[4′,5′:3,4]benzo[c]isoxazoles. Rearrangement of the latter compounds in concentrated sulfuric acid containing nitrous acid gave imidazo[4,5-a]acridones. 3H-imidazo[4,5-a]acridines were obtained by reaction of imidazo[4,5-a]acridones in boiling POCl3. Finally, new compounds were synthesized from the reaction of 3H-imidazo[4,5-a]acridine derivatives with aromatic amines in high yields. All new compounds were fully characterized by elemental analysis, IR, NMR and mass spectroscopy data. Antibacterial activity of the new compounds was tested against a panel of strains of Gram-negative and Gram-positive bacteria species and the corresponding minimum bactericidal concentration (MBC) values were determined. Results of the antimicrobial screening tests showed that new compounds are very effective against Gram-positive bacteria and their MBC values are comparable with those of well-known antibacterial agents such as cephalexin.

Keywords

imidazo[4,5-a]acridine aromatic amines antibacterial activity MBC 

Notes

Acknowledgments

We would like to express our sincere gratitude to Research Office, Mashhad Branch, Islamic Azad University (Mashhad, Iran) for financial support of this work.

References

  1. 1.
    L. Mallu, D. Thirumalai, and I. V. Asharani, Chem. Bbiology Drug Design, 90(4), 520 – 526 (2017).CrossRefGoogle Scholar
  2. 2.
    O. A. Abd-Allah, A. A. Abdelhamid. and S. K. Mohamed, Med. Chem., 2, 2161 – 0444 (2015).Google Scholar
  3. 3.
    H. Zhou, S. Bi, Y. Wang, and J. Wu, J. Biomol. Struct. Dynam., 35(10), 2077 – 2089 (2017).CrossRefGoogle Scholar
  4. 4.
    M. Kaya, Y. Yýldýrýr, and G. Y. Celik, Pharm. Chem. J., 48(11), 722 – 726 (2015).CrossRefGoogle Scholar
  5. 5.
    K. Nowak. Revi.. J. Mol. Struct., 1146, 562 – 570 (2017).CrossRefGoogle Scholar
  6. 6.
    C. D. Fahrenholtz, S. Ding, B. W. Bernish, et al., J. Inorg. Bbiochem., 165, 170 – 180 (2016).CrossRefGoogle Scholar
  7. 7.
    Z. Yu, M. Han and J. A. Cowan, Angew. Chem. Intern. Ed., 54(6), 1901 – 1905 (2015).CrossRefGoogle Scholar
  8. 8.
    S. A. Perez, C. de Haro, C. Vicente, et al., ACS Chem. Biol., 12(6), 1524 – 1537 (2017).CrossRefGoogle Scholar
  9. 9.
    R. Kumar, A. Sharma, S. Sharma, et al., Arab. J. Chem., 10, S956 – 963 (2017).CrossRefGoogle Scholar
  10. 10.
    W. Zhang, B. Zhang, T. Yang, et al., Eur. J. Med. Chem., 116, 59 – 70 (2016).CrossRefGoogle Scholar
  11. 11.
    J. Janoèkova, J. Plšikova, J. Kašparkova, et al., Eur. J. Pharm. Sci., 76, 192 – 202 (2015).CrossRefGoogle Scholar
  12. 12.
    S. M. De Almeida, E. A. Lafayette, W. L. Silva Junior, et al.,. Int. J. Biol. Macromol., 92, 467 – 475 (2016).CrossRefGoogle Scholar
  13. 13.
    O. M. Salem, M. Vilkova, J. Janoèkova, et al., Med. Chem. Res., 26(10), 2309 – 2321 (2017).CrossRefGoogle Scholar
  14. 14.
    H. Hassanzadeh, A. R. Bahrami, H. Sadeghian, et al., Medicinal Chemistry Research, 25(9), 1852 – 1860 (2016).CrossRefGoogle Scholar
  15. 15.
    D. Posfai, A. L. Eubanks, A. I. Keim, et al., Antimicrob. Agents Chemother., AAC – 01799 (2018).Google Scholar
  16. 16.
    B. Shankar, P. Jalapathi, A. Valeru, et al., Med. Chem. Res., 26(9), 1835 – 1846 (2017).CrossRefGoogle Scholar
  17. 17.
    J. Corcoran, A. Lange, R. I. Cumming, et al., Aquatic Toxicol., 152, 57 – 65 (2014).CrossRefGoogle Scholar
  18. 18.
    Y. Hu, Y. Shen, X. Wu, et al., Eur. J. Med. Chem., 143, 958 – 969 (2018).CrossRefGoogle Scholar
  19. 19.
    M. Pordel, S. Ramezani, M. Jajarmi, and M. Sokhanvar. Rus. J. Bioorg. Chem., 42(1), 106 – 110 (2016).CrossRefGoogle Scholar
  20. 20.
    A. Sadeghian, M. Pordel, H. Safdari, et al., Med. Chem. Res., 21(11), 3897 – 3901 (2012).CrossRefGoogle Scholar
  21. 21.
    M. Rahimizadeh, M. Pordel, M. Bakavoli, et al., Monatsh. Chem. Chem. Monthly, 140(6), 633 (2009).CrossRefGoogle Scholar
  22. 22.
    L. R. Daghigh, M. Pordel, A. Davoodnia. and M. Jajarmi. Med. Chem. Res., 24(11), 3912 – 3919 (2015).CrossRefGoogle Scholar
  23. 23.
    H. Hassanzadeh, A. R. Bahrami, H. Sadeghian, et al., Med. Chem. Res., 25(9), 1852 – 1860 (2016).CrossRefGoogle Scholar
  24. 24.
    V. Maroofi, M. Pordel, H. Chegini. and S. Ramezani, J. Fluoresc., 25(5), 1235 – 1243 (2015).CrossRefGoogle Scholar
  25. 25.
    M. Rahbari, M. Pordel. and J. Chamani, Rus. J. Bioorg. Chem., 42(1), 36 – 41 (2016).CrossRefGoogle Scholar
  26. 26.
    P. Tavanaei, M. Pordel and J. Chamani, Pharm. Chem. J., 49(10), 700 – 705 (2016).CrossRefGoogle Scholar
  27. 27.
    S. Ameli, M. Pordel, A. Davoodnia. and M. Jajarmi, Rus. J. Bioorg. Chem., 43(4), 429 – 434 (2017).CrossRefGoogle Scholar
  28. 28.
    S. Ramezani, M. Pordel, and A. Davoodnia, Appl. Organomet. Chem., 32(3), e4178 (2018).CrossRefGoogle Scholar
  29. 29.
    M. M. Baf, M. Pordel, and L. R. Daghigh, Tetrahedron Lett., 55(50), 6925 – 6930 (2014).CrossRefGoogle Scholar
  30. 30.
    M. Ghaemi and M. Pordel, Chem. Heterocycl. Compd., 52(1), 52 – 57 (2016).CrossRefGoogle Scholar
  31. 31.
    P. N. Preston, Chem. Heterocycl. Compd., Benzimidazoles Cogeneric Tricyclic Compd., 40, 87 – 105 (1980).Google Scholar
  32. 32.
    S. M. Finegold and L. Garrod, Bailey & Scott′s Diagn. Microbiol., 13(8), 171 – 193 (1995).Google Scholar
  33. 33.
    M. E. Pachon-Ibanez, M. E. Jimenez-Mejias. and C. Pichardo, Antimicrob. Agents Chemother., 48, 4479 – 4481 (2004).CrossRefGoogle Scholar
  34. 34.
    Y. Cheng, R. A. Srinivasa, G. Wei-Wei, et al., Eur. J. Med. Chem., 124, 935 – 945 (2016).CrossRefGoogle Scholar
  35. 35.
    N. Ranjan, S. Sandra, F. Geraldine, et al., J. Med. Chem. 60, 4904 – 4922 (2017).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Nasrin Karimi
    • 1
  • Mehdi Pordel
    • 1
    Email author
  • Abolghasem Davoodnia
    • 1
  • Hamid Sadeghian
    • 2
  • Mina Mousavian
    • 3
  1. 1.Department of Chemistry, Mashhad BranchIslamic Azad UniversityMashhadIran
  2. 2.Department of Laboratory SciencesMashhad University of Medical SciencesMashhadIran
  3. 3.Department of ChemistryPayame Noor University of MashhadMashhadIran

Personalised recommendations