https://orcid.org/0000-0003-0887-7950
Abstract
Aim: The aim was synthesis of novel benzazoles bearing amidino and 2-hydroxyphenyl substituents to explore their biological activity. Methods: Condensation of 5-substituted salicylaldehydes and intermediates gave new benzazoles by previously published and developed procedures, which were tested for antibacterial and antiproliferative activity in vitro. Results: The best antibacterial activity showed benzimidazole with 2-imidazolinyl group 27 and benzothiazole with an unsubstituted amidine 48 (minimum inhibitory concentration 8 μg/ml). Benzothiazole 53 proved most potent at inhibiting proliferation of all cancer cells (IC50: 1.2–2.0 μM). Conclusion: Most active compounds have been recognized as lead compounds for additional optimization to improve their biological activity. The type of amidine moiety markedly influenced the biological activity. Benzothiazoles showed improved antiproliferative activity in comparison to benzimidazoles.
Supplementary data
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Author contributions
A Beč and L Racané: synthesis and structural characterization, formal analysis, writing (original draft); T Tomić: synthesis and structural characterization; L Persoons and D Daelemans: evaluation of antiproliferative activity, writing (original draft); M Banjanac and V Radovanović: evaluation of antibacterial activity, writing (original draft); M Hranjec: conceptualization, investigation, writing (original draft), supervision. All authors read and approved the final manuscript.
Acknowledgments
We greatly appreciate the financial support of the Croatian Science Foundation under the projects 4379 entitled “Exploring the antioxidative potential of benzazole scaffold in the design of novel antitumor agents”. D Daelemans and L Persoons are grateful for excellent technical assistance by J Punjwani, Y Smolders, N Van Winkel and N Willems.
Financial & competing interests disclosure
The authors gratefully acknowledge the financial support of the Croatian Science Foundation under the project HRZZ-IP-2018-01-4379. The authors have no other relevant affiliations or financial involvement with any organization or entity with a financial interest in or financial conflict with the subject matter or materials discussed in the manuscript apart from those disclosed.
No writing assistance was utilized in the production of this manuscript.