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Artículo

Indole-substituted 2,4-diamino-5,8-dihydropyrido[2,3-d]pyrimidines from one-pot process and evaluation of their ability to bind dopamine receptors

Enriz, Ricardo DanielIcon ; Tosso, Rodrigo DavidIcon ; Andujar, Sebastian AntonioIcon ; Cabedo, Nuria; Cortés, Diego; Nogueras, Manuel; Cobo, Justo; Vargas Vargas, Didier FarleyIcon ; Trilleras Vásquez, Jorge Enrique
Fecha de publicación: 12/2018
Editorial: Pergamon-Elsevier Science Ltd
Revista: Tetrahedron
ISSN: 0040-4020
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:
Química Orgánica

Resumen

A series of novel 7-indole substituted 2,4-diamino-5,8-dihydropyrido[2,3-d]pyrimidine analogous to the 2,4-diaminopteridine core were synthesized by the three-component one-pot cyclocondensation between 2,4,6-triaminopyrimidine, 3-(2-cyanoacetyl)indole and aromatic aldehydes. The reactions, which exhibited good performance, proceeded in EtOH using indium (III) chloride as catalyst under microwave irradiation, in short reaction times. On the basis of certain structural similarity of these compounds with known ligands of the D2 dopamine receptors (D2DR), the study of these compounds as possible ligands of dopamine D2 and D1 receptors was carried out. Three of them showed moderate affinity to D2-DR since the Ki D1/D2 ratio reached values of 40, 65 and 31 for compounds 4c, 4k and 4j, respectively. Finally, molecular modeling studies revealed stronger molecular interactions of such derivatives with the D2DR than with D1DR, what agrees with the experimental data, and gives an additional support to the observed selectivity to the D2DR.
Palabras clave: BIND DOPAMINE , D1 AND D2 RECEPTORS , MOLECULAR MODELING , PYRIDOPYRIMIDINE , THREE-COMPONENT SYNTHESIS
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info:eu-repo/semantics/restrictedAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)
Identificadores
URI: http://hdl.handle.net/11336/89008
DOI: https://doi.org/10.1016/j.tet.2018.10.038
URL: https://www.sciencedirect.com/science/article/pii/S0040402018312444
Colecciones
Articulos(IMIBIO-SL)
Articulos de INST. MULTIDICIPLINARIO DE INV. BIO. DE SAN LUIS
Articulos(IQUIR)
Articulos de INST.DE QUIMICA ROSARIO
Citación
Enriz, Ricardo Daniel; Tosso, Rodrigo David; Andujar, Sebastian Antonio; Cabedo, Nuria; Cortés, Diego; et al.; Indole-substituted 2,4-diamino-5,8-dihydropyrido[2,3-d]pyrimidines from one-pot process and evaluation of their ability to bind dopamine receptors; Pergamon-Elsevier Science Ltd; Tetrahedron; 74; 49; 12-2018; 7047-7057
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