Synthesis and bioactivities of 1-(4-hydroxyphenyl)-2-((heteroaryl)thio)ethanones as carbonic anhydrase I, II and acetylcholinesterase inhibitors

Authors

CEM YAMALI
HALİSE İNCİ GÜL
YELİZ DEMİR
CAVİT KAZAZ
İLHAMİ GÜLÇİN

DOI

10.3906/kim-2004-36

Abstract

The discovery of enzyme targeting inhibitors is a popular area of drug research. Biological activities of the compounds bearing phenol and heteroaryl groups make them popular groups in drug design targeting important enzymes such as acetylcholinesterase (AChE, E.C.3.1.1.7) and carbonic anhydrases (CAs, EC 4.2.1.1). 1-(4-hydroxyphenyl)-2-((aryl)thio)ethanones as possible AChE and CAs inhibitors were synthesized, and their chemical structures were confirmed by IR, $^{1}$H NMR, $^{13}$C NMR, and HRMS. The compounds 2 and 4 were found potent AChE inhibitors with the Ki values of 22.13 ± 1.96 nM and 23.71 ± 2.95 nM, respectively, while the compounds 2 (Ki $=$ 8.61 ± 0.90 nM, on hCA I) and 1 (Ki $=$ 8.76 ± 0.84 nM, on hCA II) had considerable CAs inhibitory potency. The lead compounds may help the scientists for the rational designing of an innovative class of drug candidates targeting enzyme-based diseases.

Keywords

Carbonic anhydrases, acetylcholinesterase, heterocyclic, phenol

First Page

1058

Last Page

1067

Recommended Citation

YAMALI, CEM; GÜL, HALİSE İNCİ; DEMİR, YELİZ; KAZAZ, CAVİT; and GÜLÇİN, İLHAMİ (2020) "Synthesis and bioactivities of 1-(4-hydroxyphenyl)-2-((heteroaryl)thio)ethanones as carbonic anhydrase I, II and acetylcholinesterase inhibitors," Turkish Journal of Chemistry: Vol. 44: No. 4, Article 14. https://doi.org/10.3906/kim-2004-36
Available at: https://journals.tubitak.gov.tr/chem/vol44/iss4/14