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Molecules 2012, 17(2), 1388-1407; doi:10.3390/molecules17021388
Article

Synthesis, Docking Studies and Biological Evaluation of Benzo[b]thiophen-2-yl-3-(4-arylpiperazin-1-yl)-propan-1-one Derivatives on 5-HT1A Serotonin Receptors

1,* , 2, 3, 4, 2, 1 and 1
1 Departamento de Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Casilla 233, Santiago 1, Chile 2 Departamento de Farmacia, Facultad de Química, Pontificia Universidad Católica de Chile, Casilla.306, Santiago 22, Chile 3 Departamento de Bioquímica y Biología Molecular, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Casilla 233, Santiago 1, Chile 4 Unidad de Gráfica Molecular, Departamento de Química Inorgánica y Analítica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Casilla 233, Santiago 1, Chile
* Author to whom correspondence should be addressed.
Received: 29 December 2011 / Revised: 28 January 2012 / Accepted: 30 January 2012 / Published: 3 February 2012
(This article belongs to the Section Medicinal Chemistry)
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Abstract

A series of novel benzo[b]thiophen-2-yl-3-(4-arylpiperazin-1-yl)-propan-1-one derivatives 6a–f, 7a–f and their corresponding alcohols 8a–f were synthesized and evaluated for their affinity towards 5-HT1A receptors. The influence of arylpiperazine moiety and benzo[b]thiophene ring substitutions on binding affinity was studied. The most promising analogue, 1-(benzo[b]thiophen-2-yl)-3-(4-(pyridin-2-yl)piperazin-1-yl)propan-1-one (7e) displayed micromolar affinity (Ki = 2.30 μM) toward 5-HT1A sites. Docking studies shed light on the relevant electrostatic interactions which could explain the observed affinity for this compound.
Keywords: arylpiperazines; benzo[b]thiophene; depression; 5-HT1A receptor; docking; microwave Michael addition arylpiperazines; benzo[b]thiophene; depression; 5-HT1A receptor; docking; microwave Michael addition
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Pessoa-Mahana, H.; Recabarren-Gajardo, G.; Temer, J.F.; Zapata-Torres, G.; Pessoa-Mahana, C.D.; Barría, C.S.; Araya-Maturana, R. Synthesis, Docking Studies and Biological Evaluation of Benzo[b]thiophen-2-yl-3-(4-arylpiperazin-1-yl)-propan-1-one Derivatives on 5-HT1A Serotonin Receptors. Molecules 2012, 17, 1388-1407.

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