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Synthesis and biological evaluation of new naphtho- and quinolinocyclopentane derivatives as potent melatoninergic (MT 1 /MT 2 ) and serotoninergic (5-HT 2C ) dual ligands.
European Journal of Medicinal Chemistry 2017 December 2
We recently reported a series of naphthofuranic compounds as constrained agomelatine analogues. Herein, in order to explore alternative ethyl amide side chain rigidification, naphthocyclopentane and quinolinocyclopentane derivatives with various acetamide modulations were synthesized and evaluated at both melatonin (MT1 , MT2 ) and serotonin (5-HT2C ) receptors. These modifications has led to compounds with promising dual affinity and high MTs receptors agonist activity. Enantiomeric separation was then performed on selected compounds allowing us to identify levogyre enantiomers (-)-17g and (-)-17k as the highest (MT1 , MT2 )/5-HT2C dual ligands described nowadays.
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