238765-02-1

Basic information

• Product Name: 1H-Imidazole-5-carboxaldehyde, 1-[(4-bromophenyl)methyl]-
• CAS NO: 238765-02-1
• Molecular Formula: C11H9BrN2O
• Molecular Weight: 265.109
• Mol File: 238765-02-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1H-Imidazole-5-carboxaldehyde, 1-[(4-bromophenyl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-5-carboxaldehyde, 1-[(4-bromophenyl)methyl]-(238765-02-1)
• EPA Substance Registry System: 1H-Imidazole-5-carboxaldehyde, 1-[(4-bromophenyl)methyl]-(238765-02-1)

Safety Data

• Hazardous Substances Data: 238765-02-1(Hazardous Substances Data)

Usage

Molecular structure

Contains an imidazole ring, a carboxaldehyde functional group, and a 4-bromophenylmethyl substituent.

Usage

Serves as a key intermediate in the synthesis of various pharmaceutical products and organic compounds in the pharmaceutical and research industries.

Potential applications

Drug development and research related to imidazole-based compounds.

Importance

An important building block in organic synthesis.

Unique value

Its unique structure and properties make it a valuable tool for the synthesis of complex molecules and as a versatile starting material for the development of new drugs and materials.

Upstream product

• 589-15-1 1-bromomethyl-4-bromobenzene 
• 33016-47-6 (1-tritylimidazol-4-yl)carboxaldehyde 
• 26177-44-6 4-bromobenzylamine hydrochloride 
• 220364-22-7 1-(4-Bromobenzyl)-5-hydroxymethyl-1H-imidazole 

Downstream Products

• 489409-27-0 5-{[3-(4-bromobenzyl)-3H-imidazol-4-ylmethyl]-amino}-biphenyl-2-carboxylic acid methyl ester 
• 312936-83-7 4-(1-[(4-bromophenyl)methyl]imidazol-5-ylmethyl)-1-(3-chlorophenyl)piperazin-2-one 
• 742045-40-5 1-(4-bromobenzyl)-5-(chloromethyl)-1H-imidazole 

Relevant articles and documents

Structurally simple inhibitors of lanosterol 14α-demethylase are efficacious in a rodent model of acute Chagas disease

We report structure-activity studies of a large number of dialkyl imidazoles as inhibitors of Trypanosoma cruzi lanosterol-14α-demethylase (L14DM). The compounds have a simple structure compared to posaconazole, another L14DM inhibitor that is an anti-Chagas drug candidate. Several compounds display potency for killing T. cruzi amastigotes in vitro with values of EC 50 in the 0.4-10 nM range. Two compounds were selected for efficacy studies in a mouse model of acute Chagas disease. At oral doses of 20-50 mg/kg given after establishment of parasite infection, the compounds reduced parasitemia in the blood to undetectable levels, and analysis of remaining parasites by PCR revealed a lack of parasites in the majority of animals. These dialkyl imidazoles are substantially less expensive to produce than posaconazole and are appropriate for further development toward an anti-Chagas disease clinical candidate.

Potent inhibitors of farnesyltransferase and geranylgeranyltransferase-I

Compound 1 has been shown to be a dual prenylation inhibitor with FPTase (IC50=2 nM) and GGPTase-I (IC50=95 nM). Analogues of 1, which replaced the cyanophenyl group with various biaryls, led to the discovery of highly potent dual FPTase/GGPTase-I inhibitors. 4-Trifluoromethylphenyl, trifluoropentynyl, and trifluoropentyl were identified as good p-cyano replacements.