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Design of alpha7 nicotinic acetylcholine receptor ligands using the (het)Aryl-1,2,3-triazole core: Synthesis, in vitro evaluation and SAR studies
We report here the synthesis of a large library of 1,2,3-triazole derivatives which were in vitro tested as alpha7 nAchR ligands. The SAR study revealed that several crucial factors are involved in the affinity of these compounds for alpha7 nAchR such as a (R) quinuclidine configuration and a mono C-3 quinuclidine substitution. The triazole ring was substituted by a phenyl ring bearing small OMe/CH2F groups or fluorine atom and by several heterocycles such as thiophenes, furanes, benzothiophenes or benzofuranes. Among the 30 derivatives tested, the two derivatives 10 and 39 with Ki in the nanomolar range were identified (2.3 and 3 nM respectively). They exhibited a strict selectivity toward the alpha4beta2 nicotinic receptor (up to 1 muM) but interacted with the 5HT3 receptors with Ki around 3 nM. Synthesis, SAR studies and a full description of the derivatives are reported.
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Reference£º
Quinuclidine – Wikipedia,
Quinuclidine | C7H152N | ChemSpider