Synthesis, 5-hydroxytryptamine1A receptor affinity and docking studies of 3-[3-(4-aryl-1-piperazinyl)-propyl]-1H-indole derivatives

Hernán Pessoa-Mahana; Catalina Ugarte Núñez; Ramiro Araya-Maturana; Claudio Saitz Barría; Gerald Zapata-Torres; Carlos David Pessoa-Mahana; Patricio Iturriaga-Vasquez; Jaime Mella-Raipán; Miguel Reyes-Parada; Cristian Celis-Barros

doi:10.1248/cpb.60.632

Synthesis, 5-hydroxytryptamine_1A receptor affinity and docking studies of 3-[3-(4-aryl-1-piperazinyl)-propyl]-1H-indole derivatives

Hernán Pessoa-Mahana, Catalina Ugarte Núñez, Ramiro Araya-Maturana, Claudio Saitz Barría, Gerald Zapata-Torres, Carlos David Pessoa-Mahana, Patricio Iturriaga-Vasquez, Jaime Mella-Raipán, Miguel Reyes-Parada, Cristian Celis-Barros

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11 Scopus citations

Abstract

A series of 3-[3-(4-aryl-1-piperazinyl)-propyl]-1H-indole derivatives (12a-h) was synthesized and evaluated for binding affinity at the human 5-hydroxytryptamine_1A receptor (5-HT_1AR) compounds (12b) and (12h) showed the highest 5-HT_1A receptor affinity (IC ₅₀-=15 nM). Molecular docking studies with all the compounds in a homology model of 5-HT_1A showed that the main interaction anchoring the ligand in the receptor was a charge-reinforced bond between the protonated nitrogen atom (N-4) of the piperazine ring and Aspartate^3.32.

Original language	English
Pages (from-to)	632-638
Number of pages	7
Journal	Chemical and Pharmaceutical Bulletin
Volume	60
Issue number	5
DOIs	https://doi.org/10.1248/cpb.60.632
State	Published - May 2012
Externally published	Yes

Keywords

Binding
Docking
Indolylalkylarylpiperazine
Synthesis

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Pessoa-Mahana, H., Núñez, C. U., Araya-Maturana, R., Barría, C. S., Zapata-Torres, G., Pessoa-Mahana, C. D., Iturriaga-Vasquez, P., Mella-Raipán, J., Reyes-Parada, M., & Celis-Barros, C. (2012). Synthesis, 5-hydroxytryptamine_1A receptor affinity and docking studies of 3-[3-(4-aryl-1-piperazinyl)-propyl]-1H-indole derivatives. Chemical and Pharmaceutical Bulletin, 60(5), 632-638. https://doi.org/10.1248/cpb.60.632

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title = "Synthesis, 5-hydroxytryptamine1A receptor affinity and docking studies of 3-[3-(4-aryl-1-piperazinyl)-propyl]-1H-indole derivatives",

abstract = "A series of 3-[3-(4-aryl-1-piperazinyl)-propyl]-1H-indole derivatives (12a-h) was synthesized and evaluated for binding affinity at the human 5-hydroxytryptamine1A receptor (5-HT1AR) compounds (12b) and (12h) showed the highest 5-HT1A receptor affinity (IC 50-=15 nM). Molecular docking studies with all the compounds in a homology model of 5-HT1A showed that the main interaction anchoring the ligand in the receptor was a charge-reinforced bond between the protonated nitrogen atom (N-4) of the piperazine ring and Aspartate3.32.",

keywords = "Binding, Docking, Indolylalkylarylpiperazine, Synthesis",

author = "Hern{\'a}n Pessoa-Mahana and N{\'u}{\~n}ez, {Catalina Ugarte} and Ramiro Araya-Maturana and Barr{\'i}a, {Claudio Saitz} and Gerald Zapata-Torres and Pessoa-Mahana, {Carlos David} and Patricio Iturriaga-Vasquez and Jaime Mella-Raip{\'a}n and Miguel Reyes-Parada and Cristian Celis-Barros",

year = "2012",

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doi = "10.1248/cpb.60.632",

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Pessoa-Mahana, H, Núñez, CU, Araya-Maturana, R, Barría, CS, Zapata-Torres, G, Pessoa-Mahana, CD, Iturriaga-Vasquez, P, Mella-Raipán, J, Reyes-Parada, M & Celis-Barros, C 2012, 'Synthesis, 5-hydroxytryptamine_1A receptor affinity and docking studies of 3-[3-(4-aryl-1-piperazinyl)-propyl]-1H-indole derivatives', Chemical and Pharmaceutical Bulletin, vol. 60, no. 5, pp. 632-638. https://doi.org/10.1248/cpb.60.632

TY - JOUR

T1 - Synthesis, 5-hydroxytryptamine1A receptor affinity and docking studies of 3-[3-(4-aryl-1-piperazinyl)-propyl]-1H-indole derivatives

AU - Pessoa-Mahana, Hernán

AU - Núñez, Catalina Ugarte

AU - Araya-Maturana, Ramiro

AU - Barría, Claudio Saitz

AU - Zapata-Torres, Gerald

AU - Pessoa-Mahana, Carlos David

AU - Iturriaga-Vasquez, Patricio

AU - Mella-Raipán, Jaime

AU - Reyes-Parada, Miguel

AU - Celis-Barros, Cristian

PY - 2012/5

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AB - A series of 3-[3-(4-aryl-1-piperazinyl)-propyl]-1H-indole derivatives (12a-h) was synthesized and evaluated for binding affinity at the human 5-hydroxytryptamine1A receptor (5-HT1AR) compounds (12b) and (12h) showed the highest 5-HT1A receptor affinity (IC 50-=15 nM). Molecular docking studies with all the compounds in a homology model of 5-HT1A showed that the main interaction anchoring the ligand in the receptor was a charge-reinforced bond between the protonated nitrogen atom (N-4) of the piperazine ring and Aspartate3.32.

KW - Binding

KW - Docking

KW - Indolylalkylarylpiperazine

KW - Synthesis

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Synthesis, 5-hydroxytryptamine_1A receptor affinity and docking studies of 3-[3-(4-aryl-1-piperazinyl)-propyl]-1H-indole derivatives

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Keywords

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