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https://doi.org/10.5562/cca3147

Synthesis and SAR Study of Novel Amidino 2-substituted Benzimidazoles as Potential Antibacterial Agents

Nataša Perin ; Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, P. O. Box 177, HR-10000 Zagreb, Croatia
Kristina Starčević ; Department of Animal Husbandry, Faculty of Veterinary Medicine, University of Zagreb, Heinzelova 55, HR-10000 Zagreb, Croatia
Mihaela Perić ; Department for Intercellular Communication, Center for Translational and Clinical Research, University of Zagreb School of Medicine, Šalata 2, HR-10000 Zagreb, Croatia
Hana Čipčić Paljetak ; Department for Intercellular Communication, Center for Translational and Clinical Research, University of Zagreb School of Medicine, Šalata 2, HR-10000 Zagreb, Croatia
Mario Matijašić ; Department for Intercellular Communication, Center for Translational and Clinical Research, University of Zagreb School of Medicine, Šalata 2, HR-10000 Zagreb, Croatia
Višnja Stepanić ; Division of Molecular Medicine, Laboratory for Epigenomics, Ruđer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, Croatia
Donatella Verbanac ; Department for Intercellular Communication, Center for Translational and Clinical Research, University of Zagreb School of Medicine, Šalata 2, HR-10000 Zagreb, Croatia
Grace Karminski-Zamola ; Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, P. O. Box 177, HR-10000 Zagreb, Croatia
Marijana Hranjec orcid.org/0000-0002-3994-0054 ; Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, P. O. Box 177, HR-10000 Zagreb, Croatia

Sažetak

A series of novel 2-substituted benzimidazole derivatives were synthesized and their antibacterial activity was assessed against selected Gram-positive and Gram-negative bacteria. The specific moiety at the 2-position of the benzimidazole was extensively modified with several fused heterocyclic functional groups containing nitrogen and sulfur heteroatoms. In addition, the influence of different amidino groups at the position 5 of benzimidazole scaffold was evaluated. The values of clogP (a partition coefficient) and clogD7.5 (calculated distribution coefficient, pH 7.5) were determined and the lipophilic character of compounds has been found to be important parameter for the observed activity of the tested benzimidazole derivatives against Moraxella catarrhalis. The indolo 2-substituted benzimidazole 13a demonstrated solid activity against Staphylococcus aureus (MICs 16 µg/mL) and Moraxella catarralis (MICs 2 µg/mL) and represents promising lead molecule for further optimization.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Ključne riječi

amidines; benzimidazoles; antibacterial activity; Moraxella catarrhalis; lipophilicity

Hrčak ID:

184896

URI

https://hrcak.srce.hr/184896

Datum izdavanja:

3.7.2017.

Posjeta: 2.590 *