Synthesis of Arylsulfonyl Hydrazone Derivatives: Antioxidant Activity, Acetylcholinesterase Inhibition Properties, and Molecular Docking Study

Demirci Y., Kalay E., Kara Y., Güler H. İ., Can Z., Şahin E.

ChemistrySelect, cilt.8, sa.29, 2023 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 8 Sayı: 29
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1002/slct.202301474
  • Dergi Adı: ChemistrySelect
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Anahtar Kelimeler: Acetylcholinesterase inhibition, Antioxidant activity, Docking study, DPPH- FRAP, Sulfonyl hydrazine
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

In this current paper, fifteen novel sulfonyl hydrazone derivatives have been successfully synthesized and evaluated for antioxidant activity as well as their effects on inhibitory activity toward acetylcholinesterase (AChE). By using 1H NMR, 13C NMR, FT-IR, and high-resolution mass spectrometry methods, the full characterization data of the novel compounds were obtained. The synthesized compounds capacity to inhibition glucosidase and exhibit antioxidant activity were tested in vitro. It was determined that compounds (E)-4-((2-((4-chlorophenyl)sulfonyl)hydrazone)methyl)-2-methoxyphenylfuran-2-carboxylate (21), (E)-2-methoxy-4-((2-(phenylsulfonyl)hydrazone)methyl)phenylfuran-2-carboxylate (17) and (E)-4-((2-((4-bromophenyl)sulfonyl)hydrazone)methyl)-2-methoxyphenylfuran-2-carboxylate (25) showed good antioxidant activity. Upon examining the acetylcholinesterase inhibitory activity, it was determined that compounds (E)-2-methoxy-4-((2-((4-methoxyphenyl)sulfonyl) hydrazone)methyl)phenylacetate (27) (10.39 μM), (E)-4-((2-((4-chloro phenyl)sulfonyl) hydrazone)methyl)-2-methoxyphenylfuran-2-carboxylate (21) (10.81 μM), (E)-4-((2-((4-chloro phenyl)sulfonyl)hydrazone)methyl)-2-methoxyphenyl thiophene-2-carboxylate (22) (12.92 μM) and (E)-2-methoxy-4-((2-(phenylsulfonyl)hydrazone)methyl)phenylfuran-2-carboxylate (17) (12.93 μM) showed potent inhibitory effects. Molecular docking simulations were used to investigate the interactions of novel sulfonyl hydrazone derivatives with human acetylcholinesterase protein. The ligands exhibited strong binding to the receptor protein with potent inhibition.