SYNTHESIS, CHARACTERIZATION, AND TYROSINASE INHIBITORY PROPERTIES OF BENZIMIDAZOLE DERIVATIVES

© 2014 Mert Olgun Karatas^a, Bulent Alici^a, Engin Çetinkaya^b, Çiğ dem Bilen^c, Nahit Gençer^{c, #}, and Oktay Arslan^c

^#E-mail: ngencer@balikesir.edu.tr

^aInonu University, Faculty of Arts and Sciences, Department of Chemistry 44280, Malatya, Turkey;
^bEge University, Faculty of Science, Department of Chemistry, 35100, Izmir, Turkey;
^cDepartment of Chemistry, Faculty of Art and Sciences, Balikesir University, Balikesir, 10145, Turkey

Received January 8, 2014; in final form, March 3, 2014

1-Alkylbenzimidazole and 1,3-dialkyl benzimidazolium salts were synthesized and characterized by the data of IR, ¹H NMR, ¹³C NMR spectra and elemental analyses. These compounds were investigated as tyrosinase inhibitors. Tyrosinase has been purified from banana by affinity chromatography on a Sepharose 4B gel conjugated with L-tyrosine-p-aminobenzoic acid. All the synthesized compounds inhibited the tyrosinase activity. Among the compounds studied, 1,4-di(1H-benzo[d]imidazol-1-yl)butane was found to be the most active tyrosinase inhibitor (IC₅₀ 0.31 mM).

Keywords: benzimidazole, enzymatic browning, tyrosinase inhibitors.

Биоорг. химия 2014, 40 (4): 497-502