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

J 2017

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

PADRTOVA, Tereza, Pavlina MARVANOVA, Klara ODEHNALOVA, Renata KUBINOVA, Oscar PARRAVICINI et. al.

Basic information

Original name

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

Authors

PADRTOVA, Tereza (203 Czech Republic), Pavlina MARVANOVA (203 Czech Republic), Klara ODEHNALOVA (203 Czech Republic), Renata KUBINOVA (203 Czech Republic), Oscar PARRAVICINI (32 Argentina), Adriana GARRO (32 Argentina), Ricardo D ENRIZ (32 Argentina), Otakar HUMPA (203 Czech Republic, guarantor, belonging to the institution), Michal ORAVEC (203 Czech Republic) and Petr MOKRY (203 Czech Republic)

Edition

Molecules, Mayer und Muller, 2017, 1420-3049

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10403 Physical chemistry

Country of publisher

Switzerland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 3.098

RIV identification code

RIV/00216224:14740/17:00100094

Organization unit

Central European Institute of Technology

DOI

http://dx.doi.org/10.3390/molecules22122048

UT WoS

000419242400018

Keywords in English

arylcarbonyloxyaminopropanols; tertiary amines; quaternary ammonium salts; acetylcholinesterase; butyrylcholinesterase

Abstract

V originále

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

Links

LM2011020, research and development project

Name: CEITEC ? open access

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

PADRTOVA, Tereza, Pavlina MARVANOVA, Klara ODEHNALOVA, Renata KUBINOVA, Oscar PARRAVICINI, Adriana GARRO, Ricardo D ENRIZ, Otakar HUMPA, Michal ORAVEC and Petr MOKRY. Synthesis, Analysis, Cholinesterase-Inhibiting Activity and Molecular Modelling Studies of 3-(Dialkylamino)-2-hydroxypropyl 4-[(Alkoxy-carbonyl)amino]benzoates and Their Quaternary Ammonium Salts. Molecules. Mayer und Muller, 2017, vol. 22, No 12, p. 2048-2068. ISSN 1420-3049. Available from: https://dx.doi.org/10.3390/molecules22122048.

@article{1409296,
   author = {Padrtova, Tereza and Marvanova, Pavlina and Odehnalova, Klara and Kubinova, Renata and Parravicini, Oscar and Garro, Adriana and Enriz, Ricardo D and Humpa, Otakar and Oravec, Michal and Mokry, Petr},
   article_number = {12},
   doi = {http://dx.doi.org/10.3390/molecules22122048},
   keywords = {arylcarbonyloxyaminopropanols; tertiary amines; quaternary ammonium salts; acetylcholinesterase; butyrylcholinesterase},
   language = {eng},
   issn = {1420-3049},
   journal = {Molecules},
   title = {Synthesis, Analysis, Cholinesterase-Inhibiting Activity and Molecular Modelling Studies of 3-(Dialkylamino)-2-hydroxypropyl 4-[(Alkoxy-carbonyl)amino]benzoates and Their Quaternary Ammonium Salts},
   url = {http://www.mdpi.com/1420-3049/22/12/2048},
   volume = {22},
   year = {2017}
}

TY  - JOUR
ID  - 1409296
AU  - Padrtova, Tereza - Marvanova, Pavlina - Odehnalova, Klara - Kubinova, Renata - Parravicini, Oscar - Garro, Adriana - Enriz, Ricardo D - Humpa, Otakar - Oravec, Michal - Mokry, Petr
PY  - 2017
TI  - Synthesis, Analysis, Cholinesterase-Inhibiting Activity and Molecular Modelling Studies of 3-(Dialkylamino)-2-hydroxypropyl 4-[(Alkoxy-carbonyl)amino]benzoates and Their Quaternary Ammonium Salts
JF  - Molecules
VL  - 22
IS  - 12
SP  - 2048
EP  - 2048
PB  - Mayer und Muller
SN  - 14203049
KW  - arylcarbonyloxyaminopropanols
KW  - tertiary amines
KW  - quaternary ammonium salts
KW  - acetylcholinesterase
KW  - butyrylcholinesterase
UR  - http://www.mdpi.com/1420-3049/22/12/2048
L2  - http://www.mdpi.com/1420-3049/22/12/2048
N2  - 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
ER  -

PADRTOVA, Tereza, Pavlina MARVANOVA, Klara ODEHNALOVA, Renata KUBINOVA, Oscar PARRAVICINI, Adriana GARRO, Ricardo D ENRIZ, Otakar HUMPA, Michal ORAVEC and Petr MOKRY. Synthesis, Analysis, Cholinesterase-Inhibiting Activity and Molecular Modelling Studies of 3-(Dialkylamino)-2-hydroxypropyl 4-[(Alkoxy-carbonyl)amino]benzoates and Their Quaternary Ammonium Salts. \textit{Molecules}. Mayer und Muller, 2017, vol.~22, No~12, p.~2048-2068. ISSN~1420-3049. Available from: https://dx.doi.org/10.3390/molecules22122048.

Detailed Information on Publication Record