New substituted 9-propyladenine derivatives as A2Aadenosine receptor antagonists

C. Lambertucci; M. Buccioni; D. Dal Ben; S. Kachler; G. Marucci; A. Spinaci; A. Thomas; K.-N. Klotz; R. Volpini

doi:10.1039/C5MD00034C

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New substituted 9-propyladenine derivatives as A_2Aadenosine receptor antagonists†

C. Lambertucci,

^a M. Buccioni,

^a D. Dal Ben,^a S. Kachler,^b G. Marucci,

^a A. Spinaci,

^a A. Thomas,

^a K.-N. Klotz^b and R. Volpini*^a

Author affiliations

* Corresponding authors

^a School of Pharmacy, Medicinal Chemistry Unit, University of Camerino, Via S. Agostino 1, 62032 Camerino, Italy
E-mail: rosaria.volpini@unicam.it

^b Universität Würzburg, Institut für Pharmakologie und Toxikologie, Versbacher Str. 9, Würzburg, Germany

Abstract

A new series of 9-propyladenines bearing a phenylalkylamino group in the 2-position or a phenylalkyl chain in the N⁶-position, and further substituted with a bromineatom or a 2-furyl ring in the 8-position, were synthesized and tested at human adenosine receptors. The novel compounds proved to be A_2Aadenosine receptor antagonists and some of them showed high A_2A affinity, but moderate selectivity (18: K_iA_2A = 6.6 nM). Molecular modeling studies gave some explanation of the different activities of the compounds, giving suggestions for the synthesis of new A_2Aadenosine receptor antagonists.

This article is part of the themed collection: Identification and Optimization of GPCR Ligands in the 21st Century

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Article information

DOI: https://doi.org/10.1039/C5MD00034C
Article type: Concise Article
Submitted: 24 Jan 2015
Accepted: 01 Apr 2015
First published: 02 Apr 2015

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Med. Chem. Commun., 2015,6, 963-970

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New substituted 9-propyladenine derivatives as A_2Aadenosine receptor antagonists

C. Lambertucci, M. Buccioni, D. Dal Ben, S. Kachler, G. Marucci, A. Spinaci, A. Thomas, K.-N. Klotz and R. Volpini, Med. Chem. Commun., 2015, 6, 963 DOI: 10.1039/C5MD00034C

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