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Novel silver(I) N ‐heterocyclic carbene complexes bearing 2‐(4‐hydroxyphenyl)ethyl group: Synthesis, characterization, and enzyme inhibition properties
Author(s) -
Behçet Ayten,
Aktaş Aydın,
Gök Yetkin,
Kaya Rüya,
Taslimi Parham,
Gülçin İlhami
Publication year - 2021
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4199
Subject(s) - chemistry , deprotonation , carbonic anhydrase i , carbonic anhydrase , enzyme , silver acetate , stereochemistry , proton nmr , carbene , carbonic anhydrase ii , acetylcholinesterase , medicinal chemistry , nuclear chemistry , organic chemistry , catalysis , ion
Herein, novel silver‐based N ‐heterocyclic carbene (NHC) complexes bearing 2‐(4‐hydroxyphenyl)ethyl group were synthesized. Novel Ag(I)NHC complexes were synthesized from the 2‐(4‐hydroxyphenyl)ethyl‐substituted benzimidazolium salts and silver oxide via in situ deprotonation method. The successful formation of all Ag(I)NHC complexes was proved by using 1 H NMR, 13 C NMR, FTIR spectroscopy, and elemental analysis techniques. In addition, their inhibitory effects have been investigated of these substances on acetylcholinesterase (AChE), α‐glycosidase (α‐Gly), human carbonic anhydrase I (hCA I), and human carbonic anhydrase II (hCA II) enzymes. It has been seen that all compounds have a better ability to inhibit compared with existing tried inhibitors. Among these, the best inhibitor against AChE enzyme is 1g ( K i : 9.54 ± 0.98 μM and IC 50 : 17.40), and against α‐Gly, 1c showed the highest effect ( K i 3.09 ± 0.36 μM and IC 50 7.91). The best inhibitor against hCA I and hCA II enzymes are 1c and 1g compounds. For hCA I and hCA II, IC 50 values were calculated as 17.85 and 9.06 μM and K i values were measured as 5.45 ± 2.02 and 8.99 ± 2.02 μM, respectively.