Synthesis and Aldose Reductase Inhibition Effects of Novel N-Benzyl-4-Methoxyaniline Derivatives
Cetin Bayrak1,2, Gulsah Yildizhan1, Namik Kilinc3
1Department of Chemistry, Faculty of Science, Ataturk University, Erzurum, 25240-, Turkey.
Abstract:
In the current study, starting from 4-methoxyaniline, four Schiff bases were synthesized from benzaldehydes with Br and OMe. Corresponding N-benzylanilines and their derivatives were obtained from reductions (by NaBH4 ) and substitutions (by acyl and tosyl chlorides) of these bases, respectively. The inhibitory effects of the sixteen compounds, twelve of which were novel compounds are examined. Then, we conducted molecular docking and binary QSAR studies to determine inhibitory-enzyme interactions of compounds that show an inhibitory effect. Our results reveal that methoxyanilline-derived compounds show good biological activities. The most active compound (22) has IC50 values of 2.83 μM. These novel AR enzyme inhibitors may open new avenues for better AR inhibitors in the future.
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