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.

Základní údaje

Originální název

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

Autoři

PADRTOVA, Tereza (203 Česká republika), Pavlina MARVANOVA (203 Česká republika), Klara ODEHNALOVA (203 Česká republika), Renata KUBINOVA (203 Česká republika), Oscar PARRAVICINI (32 Argentina), Adriana GARRO (32 Argentina), Ricardo D ENRIZ (32 Argentina), Otakar HUMPA (203 Česká republika, garant, domácí), Michal ORAVEC (203 Česká republika) a Petr MOKRY (203 Česká republika)

Vydání

Molecules, Mayer und Muller, 2017, 1420-3049

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10403 Physical chemistry

Stát vydavatele

Švýcarsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.098

Kód RIV

RIV/00216224:14740/17:00100094

Organizační jednotka

Středoevropský technologický institut

DOI

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

UT WoS

000419242400018

Klíčová slova anglicky

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

Štítky

OA, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 12. 3. 2018 10:27, Mgr. Pavla Foltynová, Ph.D.

Anotace

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

Návaznosti

LM2011020, projekt VaV

Název: CEITEC ? open access

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, CEITEC - open access

Citovat

PADRTOVA, Tereza, Pavlina MARVANOVA, Klara ODEHNALOVA, Renata KUBINOVA, Oscar PARRAVICINI, Adriana GARRO, Ricardo D ENRIZ, Otakar HUMPA, Michal ORAVEC a 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, roč. 22, č. 12, s. 2048-2068. ISSN 1420-3049. Dostupné z: 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 a 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, roč.~22, č.~12, s.~2048-2068. ISSN~1420-3049. Dostupné z: https://dx.doi.org/10.3390/molecules22122048.

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