Synthesis, Analysis, Cholinesterase-Inhibiting Activity and Molecular Modelling Studies of 3-(Dialkylamino)-2-hydroxypropyl 4-[(Alkoxy-carbonyl)amino]benzoates and Their Quaternary Ammonium Salts

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Authors

PADRTOVA Tereza MARVANOVA Pavlina ODEHNALOVA Klara KUBINOVA Renata PARRAVICINI Oscar GARRO Adriana ENRIZ Ricardo D HUMPA Otakar ORAVEC Michal MOKRY Petr

Year of publication 2017
Type Article in Periodical
Magazine / Source Molecules
MU Faculty or unit

Central European Institute of Technology

Citation
Web http://www.mdpi.com/1420-3049/22/12/2048
Doi http://dx.doi.org/10.3390/molecules22122048
Keywords arylcarbonyloxyaminopropanols; tertiary amines; quaternary ammonium salts; acetylcholinesterase; butyrylcholinesterase
Description Tertiary amines 3-(dialkylamino)-2-hydroxypropyl 4-[(alkoxycarbonyl)amino]benzoates and their quaternary ammonium salts were synthesized. The final step of synthesis of quaternary ammonium salts was carried out by microwave-assisted synthesis. Software-calculated data provided the background needed to compare fifteen new resulting compounds by their physicochemical properties. The acid dissociation constant (pKa) and lipophilicity index (log P) of tertiary amines were determined; while quaternary ammonium salts were characterized by software-calculated lipophilicity index and surface tension. Biological evaluation aimed at testing acetylcholinesterase and butyrylcholinesterase-inhibiting activity of synthesized compounds. A possible mechanism of action of these compounds was determined by molecular modelling study using combined techniques of docking; molecular dynamics simulations and quantum mechanics calculations
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