Skip to main content
SpringerLink
Log in

Synthesis and Antibacterial Activity of 1,2,3,4-Tetrahydro- and Pyrido[1,2-a]Benzimidazoles

  • SEARCH FOR NEW DRUGS
  • Published:
Pharmaceutical Chemistry Journal Aims and scope

We report here the synthesis of a series of different 1,2,3,4-tetrahydro- and pyrido[1,2-a]benzimidazoles and assessment of their in vitro antibacterial activity against Gram-positive (Bacillus cereus) and Gram-negative (Escherichia coli AB1157, Pseudomonas aeruginosa PAO1) bacteria. Pyrido[1,2-a]benzimidazoles were the most effective against Bacillus cereus, while 1,2,3,4-tetrahydro derivatives produced the greatest level of growth inhibition of Gram-negative (Escherichia coli AB1157) bacteria. The antibacterial activity of 2,4-dimethyl-7,8-dinitropyrido[1,2-a]benzimidazole was comparable to or exceeded the efficacy of commercial tetracycline, kanamycin, levomycetin, and erythromycin formulations. A genotoxicology test (the Allium test) was used to study the mitosis-modifying and mutagenic actions of a series of condensed azaheterocyclic compounds with marked antibacterial effects. On the basis of the antibacterial activity of some of the condensed benzimidazole derivatives containing a nodal nitrogen atom detected here and the low toxicity of similar azaheterocycles led to the conclusion that there is potential for further searches for novel antibiotics among compounds of this class.

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

Similar content being viewed by others

References

  1. A. Asadi, S. Razavi, M. Talebi, et al., Infection, 47, 13 – 23 (2019).

    Article  PubMed  Google Scholar 

  2. M. I. Hutchings, A. W. Truman, and B. Wilkinson, Curr Opinion in Microbiol, 51, 72 – 80 (2019).

    Article  CAS  Google Scholar 

  3. C. Ghosh, P. Sarkar, R. Issa, et al., Trends Microbiol., 27, 323 – 338 (2019).

    Article  CAS  PubMed  Google Scholar 

  4. F. S. G. Soliman, S. M. Rida, El-Sayed A. M. Badawy, et al., Arch. Pharm., 317, 951 – 958 (1984).

    Article  CAS  Google Scholar 

  5. M. Pieroni, S. K. Tipparaju, S. Lun, et al., ChemMedChem, 6, 334 – 342 (2011).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. C. B. Sangani, H. H. Jardosh, M. P. Patel, et al., Med. Chem. Res., 22, 3035 – 3047 (2013).

    Article  CAS  Google Scholar 

  7. H. H. Jardosh, C. B. Sangani, M. P. Patel, et al., Chin. Chem. Lett., 24, 123 – 126 (2013).

    Article  CAS  Google Scholar 

  8. H. G. Kathrotiya and M. Patel, J. Chem. Sci., 125, 993 – 1001 (2013).

    Article  CAS  Google Scholar 

  9. S. K. Patil, S. A. Nirmalkar, and H. P. Deokar, Der Pharma Chemica, 9, 84 – 88 (2017).

    CAS  Google Scholar 

  10. Russian Federation Patent No. RF 2394824; Publ. July 20, 2010; Byul. No. 20.

  11. R. S. Begunov, V. O. Sakulina, M. A. Syroeshki, et al., Mendeleev Commun., 30, 633 – 635 (2020).

    Article  CAS  Google Scholar 

  12. R. S. Begunov, A. A. Sokolov, V. O. Belova, et al., Tetrahedron Lett., 56, 5701 – 5704 (2015).

    Article  CAS  Google Scholar 

  13. R. S. Begunov, A. A. Sokolov, and S. I. Filimonov, Zh. Org. Khim., 56, 1222 – 1232 (2020).

  14. Determination of Microbial Sensitivity to Antibacterial Substances. Methodological Guideline [in Russian], Federal Center for State Epidemiological Surveillance, Russian Ministry of Health, Moscow (2004), pp 7 – 20.

  15. R. S. Begunov, A. A. Sokolov, T. V. Shebunina, et al., Toksikol. Vestn., 131(2), 35 – 39 (2015).

    Google Scholar 

  16. S. Lv, X. Han, J-YWang, et al., Angew. Chem. Int. Ed., 59(11), 583 – 11,590 (2020).

  17. A. A. Sokolov, M. A. Syroeshkin, V. N. Solkan, et al., Izv. Akad. Nauk Ser. Khim., No. 2, 372 – 380 (2014).

  18. R. S. Begunov, A. A. Sokolov, and T. V. Shebunina, Zh. Org. Khim., 49, 789 – 791 (2013).

  19. G. A. Ryzvanovich, R. S. Begunov, O. A. Rachinskaya, et al., Khim.-Farm. Zh., 45(3), 13 – 15 (2011) ; Pharm Chem J, 45(3), 141 – 143 (2011).

Download references

Author information

Authors and Affiliations

  1. P. G. Demidov Yaroslavl State University, 14 Sovetskaya Street, 150003, Yaroslavl, Russia

    R. S. Begunov, Yu. V. Zaitseva, A. A. Sokolov & D. O. Egorov

  2. Yaroslavl State Technical University, 88 Moskovskii Prospekt, 150023, Yaroslavl, Russia

    S. I. Filimonov

Authors
  1. R. S. Begunov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. V. Zaitseva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. A. Sokolov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. D. O. Egorov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. I. Filimonov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. S. Begunov.

Additional information

Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 56, No. 1, pp. 25 – 31, January, 2022.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Begunov, R.S., Zaitseva, Y.V., Sokolov, A.A. et al. Synthesis and Antibacterial Activity of 1,2,3,4-Tetrahydro- and Pyrido[1,2-a]Benzimidazoles. Pharm Chem J 56, 22–28 (2022). https://doi.org/10.1007/s11094-022-02596-0

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11094-022-02596-0

Keywords

Search

Navigation