Skip to main content
Log in

Synthesis of novel 1,2- and 2-substituted benzimidazoles with high antibacterial and antioxidant activity

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Benzimidazole derivatives are potential candidates for drug development. They are efficiently synthesized and possess various biological properties including antibacterial activity. A series of functionalized benzimidazole derivatives bearing N-(4-chloro- or fluorophenyl)pyrrolidin-2-one or N-(4-chloro- or fluorophenyl)aminobutanoic acid moiety were synthesized. Compounds possessing a very high antibacterial activity, comparable to that of a commercial antibacterial agent oxytetracycline, against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and Bacillus cereus were identified. Some of the synthesized compounds exhibited significant antioxidant activity.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1

Similar content being viewed by others

References

  1. Ajani OO, Aderohunmu DV, Ikpo CO, Adedapo AE, Olanrewaju IO (2016) Arch Pharm 349:475

    Article  CAS  Google Scholar 

  2. Bansal Y, Silakari O (2012) Bioorg Med Chem 20:6208

    Article  CAS  Google Scholar 

  3. Akhtar W, Khan MF, Verma G, Shaquiquzzaman M, Rizvi MA, Mehdi SH, Akhter M, Alam MM (2017) Eur J Med Chem 126:705

    Article  CAS  Google Scholar 

  4. Song D, Ma S (2016) ChemMedChem 11:646

    Article  CAS  Google Scholar 

  5. Bai YB, Zhang AL, Tang JJ, Gao JM (2013) J Agric Food Chem 61:2789

    Article  CAS  Google Scholar 

  6. Chandrika NT, Shrestha SK, Ngo HX, Garneau-Tsodikov S (2016) Bioorg Med Chem 24:3680

    Article  CAS  Google Scholar 

  7. Starčević K, Kralj M, Ester K, Sabol I, Grce M, Pavelić K, Karminski-Zamola G (2007) Bioorg Med Chem 15:4419

    Article  Google Scholar 

  8. Bhambra AS, Edgar M, Elsegood MRJ, Horsburgh L, Kryštof V, Lucas PD, Mojally M, Teat SJ, Warwick TG, Weaver GW, Zeinali F (2016) J Fluorine Chem 188:99

    Article  CAS  Google Scholar 

  9. Gaba M, Singh S, Mohan C (2014) Eur J Med Chem 76:494

    Article  CAS  Google Scholar 

  10. Keri RS, Rajappa CK, Patil SA, Nagaraja BM (2016) Pharmacol Rep 68:1254

    Article  CAS  Google Scholar 

  11. Tonelli M, Novelli F, Tasso B, Vazzana I, Sparatore A, Boido V, Sparatore F, La Colla P, Sanna G, Giliberti G, Busonera B, Farci P, Ibba C, Lodd R (2014) Bioorg Med Chem 22:4893

    Article  CAS  Google Scholar 

  12. Anwar M, Cowley AR, Moloney MG (2010) Tetrahedron Asymmetry 21:1758

    Article  CAS  Google Scholar 

  13. Strelciunaite V, Anusevicius K, Tumosiene I, Siugzdaite J, Jonuskiene I, Ramanauskaite I, Mickevicius V (2016) Heterocycles 92:235

    Article  CAS  Google Scholar 

  14. Tumosienė I, Jonuškienė I, Kantminienė K, Beresnevicius ZJ (2012) Monatsh Chem 143:1441

    Article  Google Scholar 

  15. Tumosienė I, Jonuškienė I, Kantminienė K, Šiugždaitė J, Mickevičius V, Beresnevičius ZJ (2016) Res Chem Intermed 42:4459

    Article  Google Scholar 

  16. Parašotas I, Urbonavičiūtė E, Anusevičius K, Tumosienė I, Jonuškienė I, Kantminienė K, Vaickelionienė R, Mickevičius V (2017) Heterocycles 94:1074

    Article  Google Scholar 

  17. Mickevicius M, Beresnevicius ZJ, Mickevicius V, Mikulskiene G (2006) Heteroatom Chem 17:47

    Article  CAS  Google Scholar 

  18. Tumosienė I, Mikulskienė G, Kantminienė K, Beresnevičius ZJ (2011) Chemija 22:65

    Google Scholar 

  19. Tumosienė I, Kantminienė K, Beresnevičius ZJ (2015) Molbank 2015:M877

    Article  Google Scholar 

  20. Sevaille L, Gavara L, Bebrone C, De Luca F, Nauton L, Achard M, Mercuri P, Tanfoni S, Borgianni L, Guyon C, Lonjon P, Turan-Zitouni G, Dzieciolowski J, Becker K, Benard L, Condon C, Maillard L, Martinez J, Frere J-M, Dideberg O, Galleni M, Docquier J-D, Hernandez J-F (2017) ChemMedChem 12:972

    Article  CAS  Google Scholar 

  21. Gülcin I, Dastan A (2007) J Enz Inhib Med Chem 226:685

    Article  Google Scholar 

  22. Özen T, Taş M (2009) J Enzyme Inhib Med Chem 24:1141

    Article  Google Scholar 

  23. López-Oviedo E, Aller AI, Martín C, Castro C, Ramirez M, Pemán JM, Cantón E, Almeida C, Martín-Mazuelos E (2006) Antimicrob Agents Chemother 50:1108

    Article  Google Scholar 

  24. Goodson B, Ehrhardt A, Ng S, Nuss J, Johnson K, Giedlin M, Yamamoto R, Krebber A, Ladner M, Giacona MB, Vitt C, Winter J (1999) Antimicrob Agents Chemother 43:1429

    CAS  Google Scholar 

  25. Balouiri M, Sadiki M, Ibnsouda SK (2016) J Pharm Anal 6:71

    Article  Google Scholar 

  26. Madhu LN, Suchetha KN, Sarojini BK (2011) Drug Invent Today 3:297

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Kristina Kantminienė.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 6201 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tumosienė, I., Peleckis, A., Jonuškienė, I. et al. Synthesis of novel 1,2- and 2-substituted benzimidazoles with high antibacterial and antioxidant activity. Monatsh Chem 149, 577–594 (2018). https://doi.org/10.1007/s00706-017-2066-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-017-2066-x

Keywords

Navigation