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2-Phenylcyclopropylmethylamine Derivatives as Dopamine D<sub>2</sub> Receptor Partial Agonists: Design, Synthesis, and Biological Evaluation

Wenzhong Yan, Luyu Fan, Jing Yu, Ruiquan Liu, Huan Wang, Liang Tan, Sheng Wang, Jianjun Cheng

2021Journal of Medicinal Chemistry15 citationsDOIOpen Access PDF

Abstract

Partial agonist activity at the dopamine D2 receptor (D2R) is the primary pharmacological feature of the third-generation antipsychotics─aripiprazole, brexpiprazole, and cariprazine. However, all these drugs share a common phenyl-piperazine moiety as the primary pharmacophore. In this study, we designed and synthesized a series of novel compounds based on the 2-phenylcyclopropylmethylamine (PCPMA) scaffold and studied their pharmacological activity at the D2R. A number of potent D2R partial agonists were identified through binding affinity screening and functional activity profiling in both G protein and β-arrestin assays. The structure–functional activity relationship results showed that the spacer group is crucial for fine-tuning the intrinsic activity of these compounds. Compounds (+)-14j and (+)-14l showed good pharmacokinetic properties and an unexpected selectivity against the serotonin 2A (5-HT2A) receptor. Preliminary suppressive effects in a mouse hyperlocomotion model proved that these PCPMA-derived D2R partial agonists are effective as potential novel antipsychotics.

Topics & Concepts

Partial agonistChemistryDopamine receptor D2PharmacophoreAripiprazoleIntrinsic activityAgonistPharmacologyStereochemistryReceptorBiochemistryPsychologySchizophrenia (object-oriented programming)PsychiatryMedicineReceptor Mechanisms and SignalingNeurotransmitter Receptor Influence on BehaviorPharmacological Receptor Mechanisms and Effects