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
Similar content being viewed by others
References
Ajani OO, Aderohunmu DV, Ikpo CO, Adedapo AE, Olanrewaju IO (2016) Arch Pharm 349:475
Bansal Y, Silakari O (2012) Bioorg Med Chem 20:6208
Akhtar W, Khan MF, Verma G, Shaquiquzzaman M, Rizvi MA, Mehdi SH, Akhter M, Alam MM (2017) Eur J Med Chem 126:705
Song D, Ma S (2016) ChemMedChem 11:646
Bai YB, Zhang AL, Tang JJ, Gao JM (2013) J Agric Food Chem 61:2789
Chandrika NT, Shrestha SK, Ngo HX, Garneau-Tsodikov S (2016) Bioorg Med Chem 24:3680
Starčević K, Kralj M, Ester K, Sabol I, Grce M, Pavelić K, Karminski-Zamola G (2007) Bioorg Med Chem 15:4419
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
Gaba M, Singh S, Mohan C (2014) Eur J Med Chem 76:494
Keri RS, Rajappa CK, Patil SA, Nagaraja BM (2016) Pharmacol Rep 68:1254
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
Anwar M, Cowley AR, Moloney MG (2010) Tetrahedron Asymmetry 21:1758
Strelciunaite V, Anusevicius K, Tumosiene I, Siugzdaite J, Jonuskiene I, Ramanauskaite I, Mickevicius V (2016) Heterocycles 92:235
Tumosienė I, Jonuškienė I, Kantminienė K, Beresnevicius ZJ (2012) Monatsh Chem 143:1441
Tumosienė I, Jonuškienė I, Kantminienė K, Šiugždaitė J, Mickevičius V, Beresnevičius ZJ (2016) Res Chem Intermed 42:4459
Parašotas I, Urbonavičiūtė E, Anusevičius K, Tumosienė I, Jonuškienė I, Kantminienė K, Vaickelionienė R, Mickevičius V (2017) Heterocycles 94:1074
Mickevicius M, Beresnevicius ZJ, Mickevicius V, Mikulskiene G (2006) Heteroatom Chem 17:47
Tumosienė I, Mikulskienė G, Kantminienė K, Beresnevičius ZJ (2011) Chemija 22:65
Tumosienė I, Kantminienė K, Beresnevičius ZJ (2015) Molbank 2015:M877
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
Gülcin I, Dastan A (2007) J Enz Inhib Med Chem 226:685
Özen T, Taş M (2009) J Enzyme Inhib Med Chem 24:1141
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
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
Balouiri M, Sadiki M, Ibnsouda SK (2016) J Pharm Anal 6:71
Madhu LN, Suchetha KN, Sarojini BK (2011) Drug Invent Today 3:297
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-017-2066-x