Trimethoxycinnamates and Their Cholinesterase Inhibitory Activity

0543720 - ÚVGZ 2022 RIV CH eng J - Článek v odborném periodiku
Kos, J. - Strharsky, T. - Štěpánková, Š. - Svrčková, K. - Oravec, Michal - Hošek, J. - Imramovský, A. - Jampílek, J.
Trimethoxycinnamates and Their Cholinesterase Inhibitory Activity.
Applied Sciences-Basel. Roč. 11, č. 10 (2021), č. článku 4691. E-ISSN 2076-3417
Grant CEP: GA MŠMT(CZ) EF16_019/0000797; GA MŠMT(CZ) LM2015061
Výzkumná infrastruktura: CzeCOS III - 90123
Institucionální podpora: RVO:86652079
Klíčová slova: biological evaluation * 3,4,5-trimethoxycinnamic acid * butyrylcholinesterase * acetylcholinesterase * derivatives * design * discovery * analogs * hybrids * trimethoxycinnamates * cholinesterase-inhibiting activity * cytotoxicity * structure-activity relationships
Obor OECD: Organic chemistry
Impakt faktor: 2.838, rok: 2021
Způsob publikování: Open access
https://www.mdpi.com/2076-3417/11/10/4691

A series of twelve nature-inspired 3,4,5-trimethoxycinnamates were prepared and characterized. All compounds, including the starting 3,4,5-trimethoxycinnamic acid, were tested for their ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) in vitro, the selectivity index (SI) was also determined. 2-Fluororophenyl (2E)-3-(3,4,5-trimethoxyphenyl)-prop-2-enoate demonstrated the highest SI (1.71) in favor of BChE inhibition. 2-Chlorophenyl (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate showed the highest AChE-inhibiting (IC50 = 46.18 mu M) as well as BChE-inhibiting (IC50 = 32.46 mu M) activity with an SI of 1.42. The mechanism of action of the most potent compound was determined by the Lineweaver-Burk plot as a mixed type of inhibition. An in vitro cell viability assay confirmed the insignificant cytotoxicity of the discussed compounds on the two cell lines. Trends between structure, physicochemical properties and activity were discussed.
Trvalý link: http://hdl.handle.net/11104/0320889