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

Regular Articles

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

Author information

Hernán Pessoa-Mahana
Departments of Organic and Physical Chemistry, Faculty of Chemical and Pharmaceutical Sciences, University of Chile
Catalina Ugarte Núñez
Departments of Organic and Physical Chemistry, Faculty of Chemical and Pharmaceutical Sciences, University of Chile
Ramiro Araya-Maturana
Departments of Organic and Physical Chemistry, Faculty of Chemical and Pharmaceutical Sciences, University of Chile
Claudio Saitz Barría
Departments of Organic and Physical Chemistry, Faculty of Chemical and Pharmaceutical Sciences, University of Chile
Gerald Zapata-Torres
Analytical and Inorganic Chemistry, Faculty of Chemical and Pharmaceutical Sciences, University of Chile
Millennium Institute for Cell Dynamics and Biotechnology
Carlos David Pessoa-Mahana
Department of Pharmacy, Faculty of Chemistry, Pontificia Universidad Católica de Chile
Patricio Iturriaga-Vasquez
Millennium Institute for Cell Dynamics and Biotechnology
Department of Chemistry, Faculty of Sciences, University of Chile
Jaime Mella-Raipán
Department of Pharmacy, Faculty of Chemistry, Pontificia Universidad Católica de Chile
Miguel Reyes-Parada
Millennium Institute for Cell Dynamics and Biotechnology
School of Medicine, Faculty of Medical Sciences, University of Santiago de Chile
Facultad de Ciencias de la Salud, Universidad Autónoma de Chile
Cristian Celis-Barros
Analytical and Inorganic Chemistry, Faculty of Chemical and Pharmaceutical Sciences, University of Chile

Keywords: indolylalkylarylpiperazine, 5-hydroxytryptamine_1A receptor, docking, binding, synthesis

JOURNAL FREE ACCESS

2012 Volume 60 Issue 5 Pages 632-638

DOI https://doi.org/10.1248/cpb.60.632

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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 (IC₅₀=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.

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