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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 GABAA receptor

2006; Elsevier BV; Volume: 16; Issue: 6 Linguagem: Inglês

10.1016/j.bmcl.2005.12.037

1464-3405

Alexander C. Humphries, Emanuela Gancia, Myra T. Gilligan, Simon Goodacre, David J. Hallett, Kevin J. Merchant, Steve Thomas,

Synthesis and biological activity

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 GABAA receptor modulator 2.