Chiral Anthranilic Amides as Potential Cholinesterase Inhibitors: Synthesis, Bioactivity Assessment, and Molecular Modeling

TUNÇ, TURGAY; ALIM, ZUHAL; Kılınç, Namık; DEMİREL, NADİR

doi:10.1002/cbdv.202500974

Chiral Anthranilic Amides as Potential Cholinesterase Inhibitors: Synthesis, Bioactivity Assessment, and Molecular Modeling

Yazarlar (4)

Doç. Dr. Turgay TUNÇ Kırşehir Ahi Evran Üniversitesi, Türkiye

Prof. Dr. Zuhal ALIM Kırşehir Ahi Evran Üniversitesi, Türkiye

Namık Kılınç
Iğdır Üniversitesi, Türkiye

Prof. Dr. Nadir DEMİREL Kırşehir Ahi Evran Üniversitesi, Türkiye

Makale Türü	Özgün Makale (SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale)
Dergi Adı	Chemistry and Biodiversity (Q3)
Dergi ISSN	1612-1872 Wos Dergi Scopus Dergi
Dergi Tarandığı Indeksler	SCI-Expanded
Makale Dili	Türkçe	Basım Tarihi	07-2025
Cilt / Sayı / Sayfa	22 / 11 / –	DOI	10.1002/cbdv.202500974
Makale Linki	https://doi.org/10.1002/cbdv.202500974

Özet

Inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) are central therapeutic targets for Alzheimer's disease (AD). In this study, novel chiral anthranilic amide derivatives (5a--5d, 7a, and 7b) were synthesized from chiral amines and were characterized by ¹H, ¹³C NMR, LC--MS, and IR, then inhibitory effect of 5a--5d, 7a, and 7b on AChE/BChE activity was investigated by in vitro inhibition and in silico studies. For AChE, IC50 values of 5a--5d, 7a, and 7b were found to be 70, 63.64, 53.85, 36.84, 17.07, and 17.5 nM, respectively. For BChE, IC50 values of 5a--5d, 7a, and 7b were found as 46.66 µM, 33.33 µM, 116.6 µM, 233.3 µM, 175 nM and, 116.6 nM, respectively. All compounds had better inhibition effects against AChE than BChE. The enantioselective inhibition was observed in the compounds 5a--5d. For AChE, the S-enantiomers exhibited stronger inhibition than the R-enantiomers. However, in the case of BChE, R-enantiomers had better inhibition effects. Although molecules 7a and 7b had a stronger inhibition effect than molecules 5a--5d for AChE and BChE, the enantioselectivity was decreased in these molecules. This result was attributed to the spacer group effect in 7a and 7b.

Anahtar Kelimeler

acetylcholinesterase | butyrylcholinesterase | chiral anthranilic amide | inhibition | molecular docking

BM Sürdürülebilir Kalkınma Amaçları

Atıf Sayıları
SCOPUS	1

Chiral Anthranilic Amides as Potential Cholinesterase Inhibitors: Synthesis, Bioactivity Assessment, and Molecular Modeling

Dergi Adı	CHEMISTRY & BIODIVERSITY
Yayıncı	Wiley-Blackwell
Açık Erişim	Hayır
ISSN	1612-1872
E-ISSN	1612-1880
CiteScore	3,5
SJR	0,425
SNIP	0,700

Chiral Anthranilic Amides as Potential Cholinesterase Inhibitors: Synthesis, Bioactivity Assessment, and Molecular Modeling

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