Medicinal Chemistry Research

, Volume 25, Issue 7, pp 1316–1328 | Cite as

HQSAR and molecular docking studies of furanyl derivatives as adenosine A2A receptor antagonists

  • Camila Muñoz-Gutiérrez
  • Julio Caballero
  • Alejandro Morales-BayueloEmail author
Original Research


Structure- and ligand-based computational design strategies were used to understand the molecular requirements of furanyl derivatives 2-(furan-2-yl)-[1,2,4]triazolo[1,5-f]pyrimidin-5-amines (TfPAs), 2-(furan-2-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine (TaPAs), and 2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amines (TTAs) as adenosine A2A receptor (A2AR) antagonists. First, we studied the structure–activity relationship of the selected compounds using hologram quantitative structure–activity relationship (HQSAR) methodology. The best model (training set included 67 compounds) included fragment parameters such as atoms (A), bonds (B), connections (C), and donors/acceptors groups (DA) and had a good q 2 value of 0.776 including size fragments of 7–10 and the hologram length of 199. It also predicted adequately the compounds contained in the test set (10 compounds). In addition, we studied the binding orientations of the higher and less active compounds using flexible molecular docking. We found orientations that are in agreement with previous reports.


Parkinson’s disease Adenosine (A2A) receptor HQSAR Molecular docking 



A. M. B. thanks to the Universidad de Talca (CBSM) for the continuous support to this investigation, to the postdoctoral Project No. 3150035 (FONDECYT, CHILE). C. M. G. acknowledges support from doctoral fellowship CONICYT-PCHA/Folio 21120214. J. C. acknowledges funds of the Project FONDECYT 1130141.

Supplementary material

44_2016_1575_MOESM1_ESM.doc (64 kb)
Supplementary material 1 (DOC 63 kb)


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Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • Camila Muñoz-Gutiérrez
    • 1
  • Julio Caballero
    • 1
  • Alejandro Morales-Bayuelo
    • 1
    Email author
  1. 1.Centro de Bioinformática y Simulación Molecular (CBSM), Facultad de IngenieríaUniversidad de TalcaTalcaChile

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