Synthesis and Aldose Reductase Inhibition Effects of Novel N-Benzyl-4-Methoxyaniline Derivatives

Bayrak C., Yildizhan G., Kilinc N., Durdagi S., MENZEK A.

Chemistry and Biodiversity, cilt.19, sa.1, 2022 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 19 Sayı: 1
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1002/cbdv.202100530
  • Dergi Adı: Chemistry and Biodiversity
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aquatic Science & Fisheries Abstracts (ASFA), CAB Abstracts, Chemical Abstracts Core, EMBASE, MEDLINE, Veterinary Science Database
  • Anahtar Kelimeler: aldose reductase, bromophenol derivatives, molecular docking, N-substituted anilines, molecular modeling, ANTICHOLINERGIC ACTIVITIES, POLYOL PATHWAY, 1ST SYNTHESIS, BROMOPHENOLS, AMINATION, ALDEHYDES, FRAGMENT, BENZENE, KETONES, ENZYME
  • Atatürk Üniversitesi Adresli: Evet

Özet

© 2021 Wiley-VHCA AG, Zurich, Switzerland.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.