4-(3-Aminoazetidin-1-yl)pyrimidin-2-amines as High-Affinity Non-imidazole Histamine H3 Receptor Agonists with in Vivo Central Nervous System Activity
pmid: 31675226
pmc: PMC6912857
4-(3-Aminoazetidin-1-yl)pyrimidin-2-amines as High-Affinity Non-imidazole Histamine H3 Receptor Agonists with in Vivo Central Nervous System Activity
Despite the high diversity of histamine H3 receptor (H3R) antagonist/inverse agonist structures, partial or full H3R agonists have typically been imidazole derivatives. An in-house screening campaign intriguingly afforded the non-imidazole 4-(3-azetidin-1-yl)pyrimidin-2-amine 11b as a partial H3R agonist. Here, the design, synthesis, and structure-activity relationships of 11b analogues are described. This series yields several non-imidazole full agonists with potencies varying with the alkyl substitution pattern on the basic amine following the in vitro evaluation of H3R agonism using a cyclic adenosine monophosphate response element-luciferase reporter gene assay. The key compound VUF16839 (14d) combines nanomolar on-target activity (pKi = 8.5, pEC50 = 9.5) with weak activity on cytochrome P450 enzymes and good metabolic stability. The proposed H3R binding mode of 14d indicates key interactions similar to those attained by histamine. In vivo evaluation of 14d in a social recognition test in mice revealed an amnesic effect at 5 mg/kg intraperitoneally. The excellent in vitro and in vivo pharmacological profiles and the non-imidazole structure of 14d make it a promising tool compound in H3R research.
- Vrije Universiteit Amsterdam Netherlands
- New York University Italy
- University of Florence Italy
- Jagiellonian University Poland
- University of California, San Diego United States
Behavior, Animal, Molecular Structure, histamine, H3 receptor agonist, social memory, PHARMACOLOGICAL ASPECTS; BINDING; INHIBITION; POTENT; LIGANDS; ANTAGONISTS; ACTIVATION; DISCOVERY; FRAGMENT; IDENTIFICATION, Protein Conformation, Histamine Agonists, Molecular Docking Simulation, Mice, HEK293 Cells, SDG 3 - Good Health and Well-being, Memory, Animals, Humans, Amines, Social Behavior, Protein Binding
Behavior, Animal, Molecular Structure, histamine, H3 receptor agonist, social memory, PHARMACOLOGICAL ASPECTS; BINDING; INHIBITION; POTENT; LIGANDS; ANTAGONISTS; ACTIVATION; DISCOVERY; FRAGMENT; IDENTIFICATION, Protein Conformation, Histamine Agonists, Molecular Docking Simulation, Mice, HEK293 Cells, SDG 3 - Good Health and Well-being, Memory, Animals, Humans, Amines, Social Behavior, Protein Binding
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