1632-82-2

Usage

Chemical class

Imidazole class of organic compounds

Physical state

White to light yellow solid at room temperature

Uses

Pharmaceutical intermediate in the synthesis of various drugs and other bioactive compounds

Molecular weight

240.31 g/mol

Interaction with biological targets

Known for its ability to interact with enzymes, receptors, and other proteins

Importance in medicinal chemistry

Valuable building block in medicinal chemistry and drug discovery

Versatility

Versatile reagent in organic synthesis

Potential applications

Material science and other industrial processes

Upstream product

• 74-96-4 ethyl bromide 
• 668-94-0 4,5-diphenyl-1H-imidazole 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 100-52-7 benzaldehyde 
• 134-81-6 benzil 

Relevant academic research and scientific papers

NHC gold halide complexes derived from 4,5-diarylimidazoles: Synthesis, structural analysis, and pharmacological investigations as potential antitumor agents

A series of novel neutral NHC gold halide complexes derived from 4,5-diarylimidazoles were synthesized, characterized, and analyzed for biological effects. High growth inhibitory effects in MCF-7 and MDA-MB 231 breast cancer as well as HT-29 colon cancer cell lines depended on the presence of the C4,C5-standing aromatic rings. Methoxy groups at these rings did not change the growth inhibitory properties, while F-substituents in the ortho-position (5d) increased the activity in MCF-7 and MDA-MB 231 cells. The substituents at the nitrogen atoms and the oxidation state of the metal play a subordinate role. The most active bromo[1,3-diethyl-4,5-bis(2-fluorophenyl)-1,3- dihydro-2H-imidazol-2-ylidene]gold(I) (5d) was distinctly more active than cisplatin. All complexes caused thioredoxin reductase (TrxR) inhibition (EC 50 = 374-1505 nM) distinctly lower than auranofin (EC50 = 18.6 nM) excluding this enzyme as main target. Because of the low nuclear content, a participation of DNA interaction on the mode of action is very unlikely. The missing ER binding and the missing correlation of growth inhibition and inactivation of COX enzymes exclude these targets, too. (Figure presented)

Syntheses and analgesic activities of some 2-substituted-4,5-diphenyl and 1,2-disubstituted-4,5-diphenyl imidazole derivatives

Some substituted imidazole compounds were synthesized and their analgesic activities were determined on the Swiss albino mice (25-35 g) of either sex. During the synthesis, 2-substituted-4,5-diphenyl imidazole compounds were obtained by the reaction of benzil with some substituted or nonsubstituted aldehyde derivatives, in the presence of ammonium acetate. 1- Ethyl-2-substituted-4,5-diphenyl imidazole compounds were obtained by the reaction of purified 2-substituted-4,5-diphenyl imidazole derivatives with alkyl halides in THF at the presence of NaH. All spectral and elemental analyses of the compounds were completed and their structures elucidated. Analgesic activities of the compounds were examined using the Tail-Clip method. 15a (2-p-chlorophenyl-4,5-diphenyl imidazole) and 6b (1-ethyl-2-p- hydroxyphenyl-4,5-diphenyl imidazole) derivatives were found to be more active than the others and their LD50 values were found to be greater than 100 mg/kg (i.p.).