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Molecules 2014, 19(3), 2842-2861; doi:10.3390/molecules19032842
Article

3D-QSAR/CoMFA-Based Structure-Affinity/Selectivity Relationships of Aminoalkylindoles in the Cannabinoid CB1 and CB2 Receptors

1,* , 1, 2 and 3
1 Departamento de Química y Bioquímica, Facultad de Ciencias, Universidad de Valparaíso, Av. Gran Bretaña 1111, Playa Ancha, Valparaíso, Casilla 5030, Chile 2 Laboratorio de Bionanotecnología, Departamento de Ciencias Químico Biológicas, Universidad Bernardo O´Higgins, General Gana 1780, Santiago 8370993, Chile 3 Departamento de Farmacia, Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, 22, Santiago 7820436, Chile
* Author to whom correspondence should be addressed.
Received: 15 January 2014 / Revised: 25 February 2014 / Accepted: 25 February 2014 / Published: 5 March 2014
(This article belongs to the Section Medicinal Chemistry)
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Abstract

A 3D-QSAR (CoMFA) study was performed in an extensive series of aminoalkylindoles derivatives with affinity for the cannabinoid receptors CB1 and CB2. The aim of the present work was to obtain structure-activity relationships of the aminoalkylindole family in order to explain the affinity and selectivity of the molecules for these receptors. Major differences in both, steric and electrostatic fields were found in the CB1 and CB2 CoMFA models. The steric field accounts for the principal contribution to biological activity. These results provide a foundation for the future development of new heterocyclic compounds with high affinity and selectivity for the cannabinoid receptors with applications in several pathological conditions such as pain treatment, cancer, obesity and immune disorders, among others.
Keywords: cannabinoid; CB1/CB2; aminoalkylindole; molecular modelling; 3D-QSAR; Comparative Molecular Field Analysis (CoMFA); simulated annealing, structure-activity relationships cannabinoid; CB1/CB2; aminoalkylindole; molecular modelling; 3D-QSAR; Comparative Molecular Field Analysis (CoMFA); simulated annealing, structure-activity relationships
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

Mella-Raipán, J.; Hernández-Pino, S.; Morales-Verdejo, C.; Pessoa-Mahana, D. 3D-QSAR/CoMFA-Based Structure-Affinity/Selectivity Relationships of Aminoalkylindoles in the Cannabinoid CB1 and CB2 Receptors. Molecules 2014, 19, 2842-2861.

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