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Issue 12, 2005
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New pyrazolo[3,4-b]pyridones as selective A1 adenosine receptor antagonists: synthesis, biological evaluation and molecular modelling studies

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Abstract

A series of ethyl 4-amino-1-(2-chloro-2-phenylethyl)-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylates (5a–j) has been synthesized as potential A1 adenosine receptor (A1 AR) ligands. Binding affinities of the new compounds were determined for adenosine A1, A2A and A3 receptors. Compounds 5b and 5g showed good affinity (Ki = 299 nM and 517 nM, respectively) and selectivity towards A1 AR, whereas 5f showed good affinity for A2A AR (Ki = 290 nM), higher than towards A1 AR (Ki = 1000 nM). The only arylamino derivative of the series 5j displayed high affinity (Ki = 4.6 nM) and selectivity for A3 AR. Molecular modelling and 3D-QSAR (CoMFA) studies carried out on the most active compounds gave further support to the pharmacological results.

Graphical abstract: New pyrazolo[3,4-b]pyridones as selective A1 adenosine receptor antagonists: synthesis, biological evaluation and molecular modelling studies

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Publication details

The article was received on 24 Feb 2005, accepted on 28 Apr 2005 and first published on 19 May 2005


Article type: Paper
DOI: 10.1039/B502831K
Org. Biomol. Chem., 2005,3, 2262-2270

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    New pyrazolo[3,4-b]pyridones as selective A1 adenosine receptor antagonists: synthesis, biological evaluation and molecular modelling studies

    P. Fossa, M. Pestarino, G. Menozzi, L. Mosti, S. Schenone, A. Ranise, F. Bondavalli, M. L. Trincavelli, A. Lucacchini and C. Martini, Org. Biomol. Chem., 2005, 3, 2262
    DOI: 10.1039/B502831K

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