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Molecules 2013, 18(4), 3972-4001; doi:10.3390/molecules18043972

Design, Synthesis, Binding and Docking-Based 3D-QSAR Studies of 2-Pyridylbenzimidazoles—A New Family of High Affinity CB1 Cannabinoid Ligands

1
Departamento de Química y Bioquímica, Facultad de Ciencias, Universidad de Valparaíso, Casilla 5030, Avda. Gran Bretaña 1111, Playa Ancha, Valparaíso, Chile
2
Departamento de Farmacia, Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, 22, Santiago, Chile
3
Departamento de Química Orgánica y Físicoquímica, Facultad de Química y Ciencias Farmacéuticas, Universidad de Chile, Casilla 233, Santiago, Chile
4
Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 233, Santiago, Chile
*
Author to whom correspondence should be addressed.
Received: 26 February 2013 / Revised: 24 March 2013 / Accepted: 1 April 2013 / Published: 4 April 2013
(This article belongs to the Section Medicinal Chemistry)
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Abstract

A series of novel 2-pyridylbenzimidazole derivatives was rationally designed and synthesized based on our previous studies on benzimidazole 14, a CB1 agonist used as a template for optimization. In the present series, 21 compounds displayed high affinities with Ki values in the nanomolar range. JM-39 (compound 39) was the most active of the series (KiCB1 = 0.53 nM), while compounds 31 and 44 exhibited similar affinities to WIN 55212-2. CoMFA analysis was performed based on the biological data obtained and resulted in a statistically significant CoMFA model with high predictive value (q2 = 0.710, r2 = 0.998, r2pred = 0.823).
Keywords: cannabinoid; CB1 receptor; binding; docking; 3D-QSAR cannabinoid; CB1 receptor; binding; docking; 3D-QSAR
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Mella-Raipán, J.A.; Lagos, C.F.; Recabarren-Gajardo, G.; Espinosa-Bustos, C.; Romero-Parra, J.; Pessoa-Mahana, H.; Iturriaga-Vásquez, P.; Pessoa-Mahana, C.D. Design, Synthesis, Binding and Docking-Based 3D-QSAR Studies of 2-Pyridylbenzimidazoles—A New Family of High Affinity CB1 Cannabinoid Ligands. Molecules 2013, 18, 3972-4001.

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