143426-41-9

Usage

Chemical class

benzimidazoles

Molecular structure

a benzene ring fused to an imidazole ring, with a 2,4-dimethoxyphenyl group attached to the imidazole ring

Pharmacological activities

a potent and selective inhibitor of a specific enzyme, potential for the treatment of certain diseases

Synthesis

used as a building block in the synthesis of various pharmaceuticals and biologically active molecules

Research tool

valuable for research in the fields of medicinal chemistry and drug discovery.

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 7314-44-5 2,4-dimethoxylbenzyl alcohol 
• 88-74-4 2-nitro-aniline 
• 20781-20-8 2,4-Dimethoxybenzylamine 
• 730-29-0 N-(4-nitrobenzylidene)-benzene-1,2-diamine 
• 119386-71-9 2,2’-((1R,2R)-1,2-diaminoethane-1,2-diyl)diphenol 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-52-7 benzaldehyde 
• 555-16-8 4-nitrobenzaldehdye 
• 104-88-1 4-chlorobenzaldehyde 
• 104-87-0 4-methyl-benzaldehyde 
• 91-52-1 2,4 dimethoxybenzoic acid 

Relevant academic research and scientific papers

Nickel catalyzed sustainable synthesis of benzazoles and purines: Via acceptorless dehydrogenative coupling and borrowing hydrogen approach

Herein we report nickel-catalyzed sustainable synthesis of a few chosen five-membered fused nitrogen heterocycles such as benzimidazole, purine, benzothiazole, and benzoxazole via acceptorless dehydrogenative functionalization of alcohols. Using a bench stable, easy to prepare, and inexpensive Ni(ii)-catalyst, [Ni(MeTAA)] (1a), featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)), a wide variety of polysubstituted benzimidazole, purine, benzothiazole, and benzoxazole derivatives were prepared via dehydrogenative coupling of alcohols with 1,2-diaminobenzene, 4,5-diaminopyrimidine, 2-aminothiphenol, and 2-aminophenol, respectively. A wide array of benzimidazoles were also prepared via a borrowing hydrogen approach involving alcohols as hydrogen donors and 2-nitroanilines as hydrogen acceptors. A few control experiments were performed to understand the reaction mechanism.

Visible light promoted tandem dehydrogenation-deaminative cyclocondensation under aerobic conditions for the synthesis of 2-aryl benzimidazoles/quinoxalines fromortho-phenylenediamines and arylmethyl/ethyl amines

Visible light promoted domino synthesis of 2-aryl benzimidazoles is reported through the reaction ofortho-phenylenediamines and arylmethyl amines under aerobic conditions. The methodology has wide substrate scope and tolerates a wide range of functional groups affording the products in high yields. The use of arylethyl amines instead of arylmethyl amines gives 2-aryl quinoxalines.

Three-Way Chemoselectivity Switching through Coupled Equilibria

Controlling the chemoselectivity of reactions operating on complex mixtures, including those found in biological and petrochemical feedstocks or in the primordial soup from which life emerged, is generally challenging. The selectivity of imine oxidation c

Benzimidazoles from Aryl Alkyl Ketones and 2-Amino Anilines by an Iodine Catalyzed Oxidative C(CO)-C(alkyl) Bond Cleavage

Novel molecular iodine catalyzed cyclization reactions of 2-amino anilines with aryl alkyl ketones under oxidant and metal-free conditions are described. The reaction likely involves sequential C-N bond formation followed by C(CO)-C(alkyl) bond cleavage. Various 2-substituted benzimidazoles are obtained in moderate to good yields in a single step from readily available acetophenones, propiophenones, and phenylacetophenones.

Kinetically controlled simplification of a multiresponsive [10 × 10] dynamic imine library

Kinetically controlled self-sorting processes in complex synthetic mixtures represent an important model for behaviours of biological networks, which operate far from equilibrium and without interference among simultaneous metabolic pathways. However, most of the previously reported kinetic self-sorting protocols dealt with small dynamic libraries and a single external stimulus. Here, we report the iterative simplification of a large imine dynamic combinatorial library (DCL) constructed from 10 aldehydes and 10 anilines, under the sequential influence of an oxidant, an adsorbent, and an increase in temperature. Six components of this initial DCL are mechanically isolated and amplified at least three-fold relative to their equilibrium distributions at the outset of the sorting process.

NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR

Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

Conventional and microwave-assisted synthesis of benzimidazole derivatives and their in vitro inhibition of human cyclooxygenase

A large series of 1,2-diaryl-benzimidazole and 2-aryl-1H-benzimidazole derivatives were synthesized with slight differences using both microwave irradiation and conventional heating methods. Usually higher yields and time reactions reduction were obtained

Oxidative kinetic self-sorting of a dynamic imine library

Dynamic libraries of [n × n] imine components spontaneously simplify during a slow oxidation reaction to produce only n discrete products. The selectivity of this self-sorting process is a consequence of different oxidation rates for various imines, while the dynamic nature of the library enables self-sorting to proceed with high efficiency.

A simple and convenient one-pot synthesis of benzimidazole derivatives using cobalt(II) chloride hexahydrate as catalyst

A simple and efficient method for the convenient synthesis of 2-arylbenzimidazole has been described on reaction with o-phenylenediamine and various aromatic aldehydes using cobalt(II) chloride hexahydrate as a catalyst. The method is cost-effective, high

Carboxylated, heteroaryl-substituted chalcones as inhibitors of vascular cell adhesion molecule-1 expression for use in chronic inflammatory diseases

Starting from a simple chalcone template, structure-activity relationship (SAR) studies led to a series of carboxylated, heteroaryl-substituted chalcone derivatives as novel, potent inhibitors of vascular cell adhesion molecule-1 (VCAM-1) expression. Corr