Indol-2-Carboxylic Acid Esters Containing N-Phenylpiperazine
Moiety - Preparation and Cholinesterase-inhibiting Activity

J 2020

Indol-2-Carboxylic Acid Esters Containing N-Phenylpiperazine Moiety - Preparation and Cholinesterase-inhibiting Activity

PADRTOVÁ, Tereza, Pavlína MARVANOVÁ, Renata KUBÍNOVÁ, Jozef CSÖLLEI, Oldřich FARSA et. al.

Basic information

Original name

Indol-2-Carboxylic Acid Esters Containing N-Phenylpiperazine Moiety - Preparation and Cholinesterase-inhibiting Activity

Authors

PADRTOVÁ, Tereza (203 Czech Republic, guarantor, belonging to the institution), Pavlína MARVANOVÁ (203 Czech Republic, belonging to the institution), Renata KUBÍNOVÁ (203 Czech Republic, belonging to the institution), Jozef CSÖLLEI (203 Czech Republic, belonging to the institution), Oldřich FARSA (203 Czech Republic, belonging to the institution), Tomáš GONĚC (203 Czech Republic, belonging to the institution), Klára ODEHNALOVÁ (203 Czech Republic), Radka OPATŘILOVÁ (203 Czech Republic, belonging to the institution), Jiří PAZOUREK (203 Czech Republic, belonging to the institution), Alice SYCHROVÁ (203 Czech Republic, belonging to the institution), Karel ŠMEJKAL (203 Czech Republic, belonging to the institution) and Petr MOKRÝ (203 Czech Republic, belonging to the institution)

Edition

Current organic synthesis, Sharjah, Bentham Science Publ Ltd, 2020, 1570-1794

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

30104 Pharmacology and pharmacy

Country of publisher

United Arab Emirates

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 1.975

RIV identification code

RIV/00216224:14160/20:00118112

Organization unit

Faculty of Pharmacy

DOI

http://dx.doi.org/10.2174/1570179417666200619132218

UT WoS

000590858900009

Keywords in English

Acetylcholinesterase; butyrylcholinesterase; Fischer indole synthesis; indoles; N-phenylpiperazine; T3P (R)

Abstract

V originále

The indole derivatives and the N-phenylpiperazine fragment represent interesting molecular moieties suitable for the research of new potentially biologically active compounds. This study was undertaken to identify if indol-2-carboxylic acid esters containing N-phenylpiperazine moiety possess acetyleholinesterase and butyrylcholinesterase inhibitory activity. Materials and Methods: The study dealt with the synthesis of a novel series of analogs of 1H-indole-2-carboxylic acid and 3-methyl-1H-indole-2-carboxylic acid. The structure of the derivatives was represented by the indolylcarbonyloxyaminopropanol skeleton with the attached N-phenylpiperazine or diethylamine moiety, which formed a basic part of the molecule. The final products were synthesized as dihydrochloride salts, fumaric acid salts, and quaternary ammonium salts. The first step of the synthetic pathway led to the preparation of esters of 1H-indole-2-carboxylic acid from the commercially available 1H-indole-2-carboxylic acid. The Fischer indole synthesis was used to synthesize derivatives of 3-methyl-1H-indole-2-carboxylic acid. Results and Discussion: Final 18 indolylcarbonyloxyaminopropanols in the form of dihydrochlorides, fumarates, and quaternary ammonium salts were prepared using various optimization ways. The very efficient way for the formation of 3-methyl-1H-indole-2-carboxylate (Fischer indole cyctization product) was the one-pot synthesis of phenylhydrazine with methyl 2-oxobutanoate with acetic acid and sulphuric acid as catalysts. Conclusion: Most of the derivatives comprised of an attached N-phenylpiperazine group, which formed a basic part of the molecule and in which the phenyl ring was substituted in position C-2 or C-4. The synthesized compounds were subjected to cholinesterase-inhibiting activity evaluation, by modified Ellman method. Quaternary ammonium salt of 1H-indole-2-carboxylic acid which contain N-phenylpiperazine fragment with nitro group in position C-4 (7c) demonstrated the most potent activity against acetylcholinesterase.

Citovat

PADRTOVÁ, Tereza, Pavlína MARVANOVÁ, Renata KUBÍNOVÁ, Jozef CSÖLLEI, Oldřich FARSA, Tomáš GONĚC, Klára ODEHNALOVÁ, Radka OPATŘILOVÁ, Jiří PAZOUREK, Alice SYCHROVÁ, Karel ŠMEJKAL and Petr MOKRÝ. Indol-2-Carboxylic Acid Esters Containing N-Phenylpiperazine Moiety - Preparation and Cholinesterase-inhibiting Activity. Current organic synthesis. Sharjah: Bentham Science Publ Ltd, 2020, vol. 17, No 7, p. 576-587. ISSN 1570-1794. Available from: https://dx.doi.org/10.2174/1570179417666200619132218.

@article{1738510,
   author = {Padrtová, Tereza and Marvanová, Pavlína and Kubínová, Renata and Csöllei, Jozef and Farsa, Oldřich and Goněc, Tomáš and Odehnalová, Klára and Opatřilová, Radka and Pazourek, Jiří and Sychrová, Alice and Šmejkal, Karel and Mokrý, Petr},
   article_location = {Sharjah},
   article_number = {7},
   doi = {http://dx.doi.org/10.2174/1570179417666200619132218},
   keywords = {Acetylcholinesterase; butyrylcholinesterase; Fischer indole synthesis; indoles; N-phenylpiperazine; T3P (R)},
   language = {eng},
   issn = {1570-1794},
   journal = {Current organic synthesis},
   title = {Indol-2-Carboxylic Acid Esters Containing N-Phenylpiperazine Moiety - Preparation and Cholinesterase-inhibiting Activity},
   url = {https://europepmc.org/article/med/32560608},
   volume = {17},
   year = {2020}
}

TY  - JOUR
ID  - 1738510
AU  - Padrtová, Tereza - Marvanová, Pavlína - Kubínová, Renata - Csöllei, Jozef - Farsa, Oldřich - Goněc, Tomáš - Odehnalová, Klára - Opatřilová, Radka - Pazourek, Jiří - Sychrová, Alice - Šmejkal, Karel - Mokrý, Petr
PY  - 2020
TI  - Indol-2-Carboxylic Acid Esters Containing N-Phenylpiperazine Moiety - Preparation and Cholinesterase-inhibiting Activity
JF  - Current organic synthesis
VL  - 17
IS  - 7
SP  - 576-587
EP  - 576-587
PB  - Bentham Science Publ Ltd
SN  - 15701794
KW  - Acetylcholinesterase
KW  - butyrylcholinesterase
KW  - Fischer indole synthesis
KW  - indoles
KW  - N-phenylpiperazine
KW  - T3P (R)
UR  - https://europepmc.org/article/med/32560608
L2  - https://europepmc.org/article/med/32560608
N2  - The indole derivatives and the N-phenylpiperazine fragment represent interesting molecular moieties suitable for the research of new potentially biologically active compounds. This study was undertaken to identify if indol-2-carboxylic acid esters containing N-phenylpiperazine moiety possess acetyleholinesterase and butyrylcholinesterase inhibitory activity. Materials and Methods: The study dealt with the synthesis of a novel series of analogs of 1H-indole-2-carboxylic acid and 3-methyl-1H-indole-2-carboxylic acid. The structure of the derivatives was represented by the indolylcarbonyloxyaminopropanol skeleton with the attached N-phenylpiperazine or diethylamine moiety, which formed a basic part of the molecule. The final products were synthesized as dihydrochloride salts, fumaric acid salts, and quaternary ammonium salts. The first step of the synthetic pathway led to the preparation of esters of 1H-indole-2-carboxylic acid from the commercially available 1H-indole-2-carboxylic acid. The Fischer indole synthesis was used to synthesize derivatives of 3-methyl-1H-indole-2-carboxylic acid. Results and Discussion: Final 18 indolylcarbonyloxyaminopropanols in the form of dihydrochlorides, fumarates, and quaternary ammonium salts were prepared using various optimization ways. The very efficient way for the formation of 3-methyl-1H-indole-2-carboxylate (Fischer indole cyctization product) was the one-pot synthesis of phenylhydrazine with methyl 2-oxobutanoate with acetic acid and sulphuric acid as catalysts. Conclusion: Most of the derivatives comprised of an attached N-phenylpiperazine group, which formed a basic part of the molecule and in which the phenyl ring was substituted in position C-2 or C-4. The synthesized compounds were subjected to cholinesterase-inhibiting activity evaluation, by modified Ellman method. Quaternary ammonium salt of 1H-indole-2-carboxylic acid which contain N-phenylpiperazine fragment with nitro group in position C-4 (7c) demonstrated the most potent activity against acetylcholinesterase.
ER  -

PADRTOVÁ, Tereza, Pavlína MARVANOVÁ, Renata KUBÍNOVÁ, Jozef CSÖLLEI, Oldřich FARSA, Tomáš GONĚC, Klára ODEHNALOVÁ, Radka OPATŘILOVÁ, Jiří PAZOUREK, Alice SYCHROVÁ, Karel ŠMEJKAL and Petr MOKRÝ. Indol-2-Carboxylic Acid Esters Containing N-Phenylpiperazine Moiety - Preparation and Cholinesterase-inhibiting Activity. \textit{Current organic synthesis}. Sharjah: Bentham Science Publ Ltd, 2020, vol.~17, No~7, p.~576-587. ISSN~1570-1794. Available from: https://dx.doi.org/10.2174/1570179417666200619132218.

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