238764-83-5

Upstream product

• 2746-25-0 p-Methoxybenzyl bromide 
• 33016-47-6 (1-tritylimidazol-4-yl)carboxaldehyde 
• 3034-50-2 4⁽⁵⁾formylimidazole 
• 824-94-2 p-methoxybenzyl chloride 
• 833490-36-1 [1-(4-methoxybenzyl)-1H-5-imidazolyl]methyl acetate 
• 226931-15-3 4-[1-(4-methoxybenzyl)-1H-imidazol-5-yl]methanol 

Downstream Products

• 489409-31-6 5-{[3-(4-methoxybenzyl)-3H-imidazol-4-ylmethyl]-amino}-biphenyl-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Identification of novel imidazole flavonoids as potent and selective inhibitors of protein tyrosine phosphatase

A series of imidazole flavonoids as new type of protein tyrosine phosphatase inhibitors were synthesized and characterized. Most of them gave potent protein phosphatase 1B (PTP1B) inhibitory activities. Especially, compound 11a could effectively inhibit P

Synthesis of imidazole derivatives with antimycobacterial activity

4-Substituted 1-(p-methoxybenzyl)imidazoles were designed and synthesized in order to mimic parts of the structure of highly potent antimycobacterial 6-aryl-9-(p-methoxybenzyl)purines. 4-Haloimidazoles were subjected to Pd-catalyzed cross-coupling in order to introduce a (hetero)-aryl group, or they were converted to Grignard reagents and reacted with (hetero)arylaldehydes. Further transformations of the adducts gave a variety of potential antimycobacterials with different "spacers" between the imidazole and (hetero)aryl group. The adduct from furfural was rearranged to a cyclopentenone derivative when treated with methanol under acidic conditions. Several target compounds exhibited antimycobacterial activity in vitro (IC90 13 μg/mL for the best inhibitors), but they were not as active as the most potent purines and pyrimidines synthesized before.

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 and selective farnesyl transferase inhibitors

We recently described a novel series of CA1A2X peptidomimetics as farnesyl transferase inhibitors (FTIs). These compounds possess an N-(4-piperidinyl)benzamide scaffold mimicking A1A 2 residue. Extensive exploration of structure-activity relationships revealed that replacement of cysteine by substituted benzylimidazoles provided nanomolar FTIs with in vitro activities (18e, IC50 = 4.60 nM on isolated enzyme, EC50 = 20.0 nM for growth inhibition on a tumor cell line). The molecular docking of 18e and 19e in the active site of the enzyme provided details of key interactions with the protein and showed that the methionine or phenylalanine residue fits into the aryl binding site.