57118-68-0

Usage

Molecular structure

The compound consists of a phenyl group, an imidazole ring, and an ethylamine group.

Derivative of histamine

It is a derivative of histamine, a compound involved in various physiological processes.

Potential ligand for histamine receptors

It has been studied as a potential ligand for histamine receptors in the central nervous system.

Role in neurotransmitter release

The compound has been investigated for its potential role in modulating neurotransmitter release.

Therapeutic agent for allergic reactions and inflammatory disorders

It has been explored as a potential therapeutic agent for conditions such as allergic reactions and inflammatory disorders.

Synthesis of other pharmaceutical compounds

It has been explored for its potential use in the synthesis of other pharmaceutical compounds.

Fields of interest

2-(2-phenyl-1H-imidazol-4-yl)ethylamine is of interest in the fields of pharmacology and medicinal chemistry.

Upstream product

• 1003034-18-1 N-tert-butylcarbonyl-2-iodohidtamine 
• 98-80-6 phenylboronic acid 
• 65465-66-9 2-Oxo-4-phthalimido-1-butyl acetate 
• 618-39-3 benzamidin 
• 66675-20-5 1,2,4-tris-(benzoilamino)-1-butene 
• 93-97-0 benzoic acid anhydride 

Downstream Products

• 521268-99-5 (2S)-1-{[2-(2-Phenyl-1H-imidazol-4-yl)-ethylamino]-acetyl}-pyrrolidine-2-carbonitrile 

Relevant academic research and scientific papers

Synthesis of substituted 2-phenylhistamines via a microwave promoted Suzuki coupling

Substitutions on the 2-position of the imidazole ring of histamine have proven useful in a number of biochemical settings. Current art for the synthesis of these constructs relies upon a cumbersome and low-yielding condensation reaction. Here-in we report a new procedure for the synthesis of a series of substituted 2-phenylhistamines utilizing a microwave-promoted Suzuki coupling.

Synthesis and Histamine H1 Receptor Agonist Activity of a Series of 2-Phenylhistamines, 2-Heteroarylhistamines, and Analogues

New histamine derivatives characterized by a (substituted) aryl, heteroaryl, benzyl, or hetroarylmethyl substituent in the C2 position of the imidazole ring have been prepared from appropriate imidates or amidines, respectively, and 2-oxo-4-phthalimido-1-butyl acetate (1).The compounds were screened as potential H1 receptor agonist on the isolated guinea pig ileum.The 3-halogenated 2-phenylhistamines (halogen = Br (35) and I (36) were equipotent with histamine, while 2-(3-(trifluoromethyl)phenyl)histamine (2-ethanamine (39)) was significantly more potent than histamine (39: pD2 = 6.81, relative activity = 128percent).The 2-substituted histamine analogues were potential H1 receptor agonists on the endothelium-denuded isolated guinea pig aorta with pEC50 values generally smaller than observed on the guinea pig ileum, but the rank order of potency was found to be similar.The contractile effects on guinea pig ileum and aorta, respectively, could be blocked concentraction-dependently by the H1 receptor antagonist mepyramine, yielding KB values for mepyramine in the nanomolar range.In vitro compounds 35 and 39 bound to mepyramine-labeled guinea pig cerebellar membranes with a pKi of 6.1 and 5.9, respectively.However, upon iv administration, 35 (3-100 mg/kg) and 39 (3-300 mg/kg) failed to inhibit the binding of mepyramine to mouse cerebral cortex in vivo , thereby indicating that these histamine derivatives are not able to penetrate the blood-brain berrier.In functional in vitro studies on histamine H2, H3, and other neurotransmitter receptors the selectivity of 39 was found to be 2138 (H1:H2), >64 (H1:H3), 1000 (H1:M3, 105 (H1:α1), 708 (H1:β1) and 71 (H1:5HT2A).Thus compound 39 is the most potent and selective H1 receptor agonist reported so far .These results make meta- substituted 2-phenylhistamines, especially 2-(3-(trifluoromethyl)phenyl)- and 2-(3-bromophenyl)histamine (39 and 35, respectively) valuable experimental tools for the selective stimulation of histamine H1 receptors and the study of H1 receptor-mediated functions.