8-Fluoroimidazo[1,2-a]pyridine: Synthesis, physicochemical properties and evaluation as a bioisosteric replacement for imidazo[1,2-a]pyrimidine in an allosteric modulator ligand of the GABA sub(A) receptor

8-Fluoroimidazo[1,2-a]pyridine: Synthesis, physicochemical properties and evaluation as a bioisosteric replacement for imidazo[1,2-a]pyrimidine in an allosteric modulator ligand of the GABA sub(A) receptor

8-Fluoroimidazo[1,2-a]pyridine has been established as a physicochemical mimic of imidazo[1,2-a]pyrimidine, using both in silico and traditional techniques. Furthermore, a novel synthesis of a 3,7-disubstituted-8- fluoroimidazopyridine 3 has been developed and the utility of the physicochemical mimi...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters Vol. 16; no. 6; pp. 1518 - 1522
Main Authors: Humphries, Alexander C, Gancia, Emanuela, Gilligan, Myra T, Goodacre, Simon, Hallett, David, Merchant, Kevin J, Thomas, Steve R
Format: Journal Article
Language:English
Published: 01-01-2006
Online Access:Get full text
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Summary:8-Fluoroimidazo[1,2-a]pyridine has been established as a physicochemical mimic of imidazo[1,2-a]pyrimidine, using both in silico and traditional techniques. Furthermore, a novel synthesis of a 3,7-disubstituted-8- fluoroimidazopyridine 3 has been developed and the utility of the physicochemical mimicry has been demonstrated in an in vitro system. Here, the 8-fluoroimidazopyridine ring contained in ligand 3 acts as a bioisosteric replacement for imidazopyrimidine in the GABA sub(A) receptor modulator 2.
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ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2005.12.037