Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/5938
Title: Substituted pyrazolo[3,4-b]pyridines as human A1 adenosine antagonists: developments in understanding the receptor stereoselectivity.
Authors: Tuccinardi, T
Zizzari, At
Brullo, C
Daniele, S
Musumeci, F
Schenone, S
Trincavelli, Ml
Martini, C
Martinelli, A
Giorgi, Gianluca 
Botta, Maurizio 
Issue Date: 2011
Project: None 
Journal: ORGANIC & BIOMOLECULAR CHEMISTRY
Abstract: 
A(1) adenosine 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 A(1) adenosine ligands endowed with an antagonistic profile. In the present work, we report the LC separation of enantiomers of our most active A(1) antagonists 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 A(1)AR affinity. We also developed a homology model of this receptor subtype in order to suggest a binding disposition of the ligands into the hA(1)AR. All of the obtained data suggest that the compound's chirality plays a key role in A(1) affinity.
Description: 
40547
URI: http://hdl.handle.net/20.500.12779/5938
ISSN: 1477-0520
DOI: 10.1039/C0OB01064B
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