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

Küçük Resim Yok

Tarih

2023

Dergi Başlığı

Dergi ISSN

Cilt Başlığı

Yayıncı

Wiley-V C H Verlag Gmbh

Erişim Hakkı

info:eu-repo/semantics/closedAccess

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 H-1 NMR, C-13 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 & mu;M), (E)-4-((2-((4-chloro phenyl)sulfonyl) hydrazone)methyl)-2-methoxyphenylfuran-2-carboxylate (21) (10.81 & mu;M), (E)-4-((2-((4-chloro phenyl)sulfonyl)hydrazone)methyl)-2-methoxyphenyl thiophene-2-carboxylate (22) (12.92 & mu;M) and (E)-2-methoxy-4-((2-(phenylsulfonyl)hydrazone)methyl)phenylfuran-2-carboxylate (17) (12.93 & mu;M) 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.

Açıklama

Anahtar Kelimeler

Sulfonyl hydrazine, Acetylcholinesterase inhibition, Antioxidant activity, Docking study, DPPH- FRAP

Kaynak

Chemistryselect

WoS Q Değeri

Q3

Scopus Q Değeri

Q2

Cilt

8

Sayı

29

Künye