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Issue 12, 2011
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Substituted pyrazolo[3,4-b]pyridines as human A1adenosine antagonists: Developments in understanding the receptor stereoselectivity

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Abstract

A1adenosine receptor antagonists have been proposed to possess an interesting range of potential therapeutic applications. We have already reported the synthesis and the biological characterization of a family of pyrazolo[3,4-b]pyridine derivatives as A1adenosine ligands endowed with an antagonistic profile. In the present work, we report the LC separation of enantiomers of our most active A1antagonists together with the determination of their absolute configuration by means of X-ray crystal structure analysis. Biological assays confirmed a different activity for the two enantiomers, with the R one showing the higher human A1AR affinity. We also developed a homology model of this receptor subtype in order to suggest a binding disposition of the ligands into the hA1AR. All of the obtained data suggest that the compound's chirality plays a key role in A1 affinity.

Graphical abstract: Substituted pyrazolo[3,4-b]pyridines as human A1adenosine antagonists: Developments in understanding the receptor stereoselectivity

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Supplementary files

Article information


Submitted
07 Dec 2010
Accepted
09 Feb 2011
First published
09 Mar 2011

Org. Biomol. Chem., 2011,9, 4448-4455
Article type
Paper

Substituted pyrazolo[3,4-b]pyridines as human A1adenosine antagonists: Developments in understanding the receptor stereoselectivity

T. Tuccinardi, A. T. Zizzari, C. Brullo, S. Daniele, F. Musumeci, S. Schenone, M. L. Trincavelli, C. Martini, A. Martinelli, G. Giorgi and M. Botta, Org. Biomol. Chem., 2011, 9, 4448
DOI: 10.1039/C0OB01064B

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