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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 (CC BY 3.0).
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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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