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New generation dopaminergic agents. 1. Discovery of a novel scaffold which embraces the D2 agonist pharmacophore. Structure-activity relationships of a series of 2-(aminomethyl)chromans
A series of 2-(aminomethyl)chromans (2-AMCs) was synthesized and evaluated for their affinity and selectivity for both the high- and low- affinity agonist states (D2(High) and D2(Low), respectively) of the dopamine (DA) D2 receptor. The 7-hydroxy-2-(aminomethyl)chroman moiety was observed to be the primary D2 agonist pharmacophore. The 2-methylchroman moiety was discovered to be an entirely novel scaffold which could be used to access the D2 agonist pharmacophore. Attaching various simple alkyl and arylalkyl side chains to the 7-hydroxy 2-AMC nucleus had significant effects on selectivity for the D2(High) receptor vs the 5HT(1A) and alpha1 receptors. A novel DA partial agonist, (R)-(-)-2-(benzylamino)methyl)chroman-7 ol[R-(- )-35c], was identified as having the highest affinity and best selectivity for the D2(High) receptor vs the alpha1 and 5HT(1A) receptors. Several regions of the 2-AMC nucleus were modified and recognized as potential sites to modulate the level of intrinsic activity. The global minimum conformer of the 7-hydroxy-2-AMC moiety was identified as fulfilling the McDermed model D2 agonist pharmacophoric criteria and was proposed as the D2 receptor-bound conformation. Structure-activity relationships gained from these studies have aided in the synthesis of D2 partial agonists of varying intrinsic activity levels. These agents should be of therapeutic value in treating disorders resulting form hypo- and hyperdopaminergic activity, without the side effects associated with complete D2 agonism or antagonism.
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Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics