745809-88-5

Upstream product

• 122-85-0 para-acetamidobenzaldehyde 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 75-36-5 acetyl chloride 
• 71002-88-5 5⁽⁶⁾-nitro 2-(4-aminophenyl)-1H-benzimidazole 
• 150-13-0 4-amino-benzoic acid 

Downstream Products

• 1027290-64-7 N-[4-(5-amino-1H-benzoimidazol-2-yl)-phenyl]-acetamide 
• 71002-88-5 2-(4-aminophenyl)-5⁽⁶⁾-nitrobenzimidazole 

Relevant academic research and scientific papers

Substituted 2-phenyl-benzimidazole derivatives: novel compounds that suppress key markers of allergy

The pharmacotherapy of allergy and asthma has traditionally focused on the effecter molecules of the allergic cascade, while neglecting targets that play an early role in their development. Reasoning that IgE is central to the expansion of atopic diseases, we identified and extended a novel family of 2-(substituted phenyl)-benzimidazole inhibitors of IgE response. Pharmacological activity depends on an intact phenylbenzimidazole-bis-amide backbone, and is optimized by the presence of lipophilic terminal groups composed of either bis cycloalkyl or combinations of aliphatic and halogen-substituted aromatic groups. These compounds also inhibit IL-4 and IL-5 responses in T cells and CD23 expression on B cells, with potencies that parallel their inhibition of IgE. The broad profile of these compounds thus underscores their potential for treating the multifarious pathology of asthma.

Tuning second-order optical nonlinearities in push-pull benzimidazoles

The synthesis and full characterization of new chromophores with second order optical nonlinearities containing the 2-phenyl-(5,6)-nitrobenzimidazole group is reported. Starting from 2-{4-[(4-N,N-dihydroxyethylamino)phenylazo] phenyl}-5(6)-nitrobenzimidazole, a combined theoretical and experimental approach, including theoretical computations of second order nonlinear optical activity (MNDO/AM1), X-ray structural analysis and synthetic strategies, has led to a significant optimization (more than 50%) of the NLO activity of related chromophores. The results indicate that 6-nitro-substituted compounds are more active than 5-nitro-substituted ones and that a further increase of NLO activity can be achieved by insertion of a carbon-carbon double bond between the benzimidazole and 2-phenyl rings. Calculations also suggest that an additional improvement of the nonlinearity should be expected upon functionalization of the N1 atom of the 6-nitrobenzimidazole with electron-withdrawing groups. Experimental nonlinearities (EFISH technique, μβ/ 10-48 esu, γ = 1.907 μm, DMF solution) between 940 and 1550 were measured. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).