4238-72-6

Usage

Imidazole family

Five-membered ring with nitrogen at two adjacent positions This describes the structure of the imidazole family of organic compounds, which 1H-Imidazole, 4-(phenylmethyl)is a part of.

Phenylmethyl group

Benzene ring attached to the imidazole structure This indicates the presence of a benzene ring in the compound, which is connected to the imidazole structure.

Applications

Pharmaceuticals, agrochemicals, and materials science 1H-Imidazole, 4-(phenylmethyl)is used in various industries, including the synthesis of biologically active molecules and the development of new materials.

Ligand or building block

Ability to act as a ligand or a building block in the synthesis of biologically active molecules This highlights the compound's role in creating molecules with potential biological activity.

Upstream product

• 107398-51-6 5-benzyl-N,N-dimethylimidazole-1-sulphonamide 
• 122-78-1 phenylacetaldehyde 
• 100-58-3 phenylmagnesium bromide 
• 33016-47-6 (1-tritylimidazol-4-yl)carboxaldehyde 

Downstream Products

• 57662-32-5 4-(4-nitro-benzyl)-1H-imidazole 

Relevant academic research and scientific papers

6,11-dihydro-5H-benzo[d]imidazo[1,2-a]azepines derivatives as histamine H4 receptor ligands

The present patent application concerns new ligands of the H4-receptor, their process of preparation and their therapeutic use.

Synthesis and histamine H3 receptor activity of 4-(n-alkyl)-1H-imidazoles and 4-(omega-phenylalkyl)-1H-imidazoles.

The influence of lipophilic moieties attached to a 4-1H-imidazole ring on the histamine H3 receptor activity was systematically investigated. Series of 4-(n-alkyl)-1H-imidazoles and 4-(omega-phenylalkyl)-1H-imidazoles were prepared, with an alkyl chain varying from 2-9 methylene groups and from 1-9 methylene groups, respectively. The compounds were tested for their activity on the H3 receptor under in vitro conditions. For the 4-(n-alkyl)-1H-imidazoles the activity is proportional to chain length, ranging from a pA2 value of 6.3 +/- 0.2 for 4-(n-propyl)-1H-imidazole to a pA2 value of 7.2 +/- 0.1 for 4-(n-decyl)-1H-imidazole. For the series 4-(omega-phenylalkyl)-4H-imidazoles an optimum in H3 activity was found for the pentylene spacer: 4-(omega-phenylpentyl)-1H-imidazole has a pA2 value of 7.8 +/- 0.1.

HIGH-YIELDING SYNTHESES OF 4(5)-SUBSTITUTED IMIDAZOLES VIA ORGANOLITHIUM INTERMEDIATES. THE UTILITY OF SULPHONAMIDE N-PROTECTION AND SILICON-CONTAINING BLOCKING GROUPS

N-protection of imidazole as its N,N-dimethyl-sulphonamido derivative, and blocking of the 2-position with the triethylsilyl group permits regioselective 5-metallation with sec-butyl-lithium.The resulting organolithium intermediates react with a range of electrophiles and the products are easily deprotected to give the 4(5)-substituted NH-free imidazoles in good to excellent yields.Isolation of the silicon-blocked intermediate is unnecessary and, indeed, is disadvantageous to final yields, making the procedure attractively economical of time.