1020210-48-3

Upstream product

• 67-56-1 methanol 
• 1020210-41-6 methyl 3-amino-4-[(5-tert-butyl-1H-pyrazol-3-yl)amino]-3-nitrobenzoate 
• 707-07-3 orthobenzoic acid trimethyl ester 
• 1020210-39-2 methyl 4-[(3-tert-butyl-1H-pyrazol-5-yl)amino]-3-nitrobenzoate 
• 59997-51-2 trimethylacetylacetonitrile 
• 453-71-4 3-nitro-4-fluorobenzoic acid 
• 329-59-9 4-fluoro-3-nitro-benzoic acid methyl ester 
• 82560-12-1 3-tert-butyl-1H-pyrazole-5-amine 

Relevant academic research and scientific papers

Synthesis of novel 1,2,5-trisubstituted benzimidazoles as potential antitumor agents

Novel methyl 1-(5-tert-butyl-1H-pyrazol-3-yl)-2-(aryl)-1H-benzo[d] imidazole-5-carboxylates 11 were synthesized by following a four-step strategy involving a nucleophilic aromatic displacement (SNAr) and a solvent free approach as key steps for the formation of the desired products. Structure of intermediates and products were confirmed by X-ray diffraction as well as the tautomeric rearrangement suffered by the pyrazole moiety during the curse of the final cyclization process. Several of the obtained compounds were screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Products 11b and 11n exhibited the highest activity against a range of cancer cell lines with remarkable values in panels of Non-Small Cell Lung Cancer, Melanoma and Leukemia, with GI50 range of 1.15-7.33 μM and 0.167-7.59 μM, respectively, and suitable LC 50 with values greater than 100 μM.

Solution-phase and solid-phase synthesis of 1-pyrazol-3-ylbenzimidazoles

The facile solution and solid-phase synthesis of 1-pyrazol-3- ylbenzimidazoles from 4-fluoro-3-nitrobenzoate derivatives and 5(3)-amino-3(5)-subtituted-1H-pyrazoles is reported. The key step is the unexpected nucleophilic aromatic displacement of the activated fluorine by the exocyclic amino group of the pyrazole ring leading to 4-pyrazolylamino-3- nitrobenzoate derivatives, which are easily converted into the corresponding 1-pyrazol-3-ylbenzimidazoles in very high isolated yield. These novel methodologies would be very useful for the generation of libraries of diverse 1-heteroaryl derivatives of benzimidazoles. Georg Thieme Verlag Stuttgart.