Synthesis and biological evaluation of aminomethyl and alkoxymethyl derivatives as carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase inhibitors

Abstract

Compounds containing nitrogen and sulfur atoms can be widely used in various fields such as industry, medicine, biotechnology and chemical technology. Therefore, the reactions of aminomethylation and alkoxymethylation of mercaptobenzothiazole, mercaptobenzoxazole and 2-aminothiazole were developed. Additionally, the alkoxymethyl derivatives of mercaptobenzoxazole and 2-aminothiazole were synthesized by a reaction with hemiformals, which are prepared by the reaction of alcohols and formaldehyde. In this study, the inhibitory effects of these molecules were investigated against acetylcholinesterase (AChE), butyrylcholinesterase (BChE) enzymes and carbonic anhydrase I, and II isoenzymes (hCA I and II). Both hCA isoenzymes were significantly inhibited by the recently synthesized molecules, with K values in the range of 58-157 nM for hCA I, and 81-215 nM for hCA II. Additionally, the K parameters of these molecules for BChE and AChE were calculated in the ranges 23-88 and 18-78 nM, respectively.

Preliminary phytochemical analysis and evaluation of in vitro antioxidant, antiproliferative, antidiabetic, and anticholinergics effects of endemicGypsophilataxa from Turkey

“…Inhibition of AChE and BChE enzymes which hydrolysis Ach and BCh is the most established approach for the treatment AD. AChE is exists in all excitable cells, while BChE enzyme is present more commonly in the central neural system, plasma, and liver (Gulçin et al, ).…”

Novel amides of 1,1‐bis‐(carboxymethylthio)‐1‐arylethanes: Synthesis, characterization, acetylcholinesterase, butyrylcholinesterase, and carbonic anhydrase inhibitory properties

“…A well-recorded CA inhibitor, AZA, also some other CA inhibitors such as methazolamide, topiramate, and zonisamide, were agreed for the therapy of epileptic disorders and epilepsy, and these are yet used in the absence, myoclonic, partial, and primary generalized tonicclonic seizures in composition with other antiepileptic drugs or in resistant epilepsy [45][46][47][48][49] . A well-recorded CA inhibitor, AZA, also some other CA inhibitors such as methazolamide, topiramate, and zonisamide, were agreed for the therapy of epileptic disorders and epilepsy, and these are yet used in the absence, myoclonic, partial, and primary generalized tonicclonic seizures in composition with other antiepileptic drugs or in resistant epilepsy [45][46][47][48][49] .…”

The effects of hesperidin on sodium arsenite-induced different organ toxicity in rats on metabolic enzymes as antidiabetic and anticholinergics potentials: A biochemical approach

“…Additionally, the defined key role of CA inhibitor (CAI) molecules as antiglaucoma compounds and diuretics factor, it has recently appointed which they have capability as anticonvulsant, antiobesity, antiinfective, and anticancer drugs (Gulçin et al, ; Koçyiğit, Taşkıran, et al, ; Taslimi, Osmanova, et al, ; Taslimi, Caglayan, et al, ; Yamali, Gül, Ece, Taslimi, & Gulçin, ). Indeed, there are diverse approved compounds as AChEIs like galanthamine, donepezil, tacrine molecule, and rivastigmine for the treatment of AD (Bulut et al, ).…”