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Synthesis and biological evaluation of some 1‐naphthol derivatives as antioxidants, acetylcholinesterase, and carbonic anhydrase inhibitors
Author(s) -
Erdoğan Musa,
Polat Köse Leyla,
Eşsiz Selçuk,
Gülçin İlhami
Publication year - 2021
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.202100113
Subject(s) - chemistry , acetylcholinesterase , carbonic anhydrase , carbonic anhydrase i , dpph , abts , aromatization , stereochemistry , cycloaddition , chemical synthesis , enzyme , carbonic anhydrase ii , biological activity , halogenation , medicinal chemistry , antioxidant , organic chemistry , in vitro , catalysis , biochemistry
A series of some naphthol derivatives 4a – f , 5a , f , 6a , and 7a , b (six novel ones: 4c,d , 5a , 6a , 7a,b ) bearing F, Cl, Br, OMe, and dioxole substituents at different positions of the aromatic rings was designed, synthesized, and characterized. The naphthol derivatives were synthesized in three steps, namely the addition reaction of furan via Diels–Alder cycloaddition reaction, copper(II) trifluoromethanesulfonate (Cu(OTf) 2 )‐catalyzed aromatization reaction, and the bromination reaction, respectively. The structures of the newly obtained compounds ( 4c , d , 5a , 6a , 7a , b ) were characterized by spectroscopic techniques. In addition, some biological activity studies were investigated under in vitro conditions. Inhibition studies of these compounds were performed on human carbonic anhydrase (hCA) I and II isoenzymes purified from human erythrocytes as a biological evaluation. Moreover, their potential antioxidant and antiradical activities were studied by analytical methods like ABTS •+ and DPPH• scavenging, and it was determined that some molecules showed good activity. Also, inhibition of acetylcholinesterase (AChE), which is a marker of many degenerative neurological diseases, was tested and the results were discussed. Excellent enzyme inhibition results were recorded for most of the molecules. These 1‐naphthol derivatives were found as effective inhibitors for hCA I, hCA II, and AChE with K i values ranging from 0.034 ± 0.54 to 0.724 ± 0.18 µM for hCA I, 0.172 ± 0.02 to 0.562 ± 0.21 µM for hCA II, and 0.096 ± 0.01 to 0.177 ± 0.02 µM for AChE.