1016-93-9

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
1H-Imidazo[4,5-b]pyridine, 2-phenylis used as a core structure in the development of biologically active compounds for various therapeutic applications. Its presence in anti-inflammatory, anti-cancer, and anti-viral agents highlights its potential in addressing significant health challenges.
Used in Drug Discovery:
The unique structure and biological activity of 1H-Imidazo[4,5-b]pyridine, 2-phenylmake it a valuable target for drug discovery, where it can be utilized to identify and develop new pharmaceutical agents with improved efficacy and selectivity.
Used in Organic Synthesis:
1H-Imidazo[4,5-b]pyridine, 2-phenylis used as a reagent in organic synthesis for the preparation of other imidazo[4,5-b]pyridine-based compounds. These compounds can exhibit a range of properties and potential applications, further expanding the utility of this core structure in various industries.

Upstream product

• 452-58-4 2,3-Diaminopyridine 
• 65-85-0 benzoic acid 
• 119-61-9 benzophenone 
• 495-40-9 propiophenone 
• 98-86-2 acetophenone 
• 93-55-0 1-phenyl-propan-1-one 
• 63581-31-7 N₃-benzylidenepyridine-2,3-diamine 
• 100-52-7 benzaldehyde 
• 39856-58-1 3-amino-2-bromopyridine 
• 1480-87-1 2-fluoro-3-nitropyridine 
• 100-46-9 benzylamine 
• 54231-35-5 3-fuoro-2-nitropyridine 
• 2876-13-3 N-benzylpyridinium chloride 
• 127896-76-8 N-(1-chlorobenzyl)pyridinium chloride 

Relevant academic research and scientific papers

Rapid synthesis of imidazo[4,5-b]pyridine containing polycyclics by means of palladium-catalyzed amidation of 2-chloro-3-nitropyridine

Regioselective nucleophilic substitution of 2-chloro 3-nitropyridine with heterocyclic amides under Pd-catalyzed reaction conditions as described by Buchwald yielded imidazo [4,5-b] pyridine-containing polycyclics as novel scaffolds.

Aqueous synthesis of 1-H-2-substituted benzimidazoles via transition-metal-free intramolecular amination of aryl iodides

A straightforward method has been developed for the synthesis of the benzimidazole ring system through a carbon-nitrogen cross-coupling reaction. In the presence of 2.0 equiv. of K2CO3 in water at 100 °C for 30 h, the intramolecular cyclization of N-(2-iodoaryl)benzamidine provides benzimidazole derivatives in moderate to high yields. Remarkably, the procedure occurs exclusively in water and doesn't require the use of any additional reagent/catalyst, rendering the methodology highly valuable from both environmental and economical points of view.

Sodium sulfide: A sustainable solution for unbalanced redox condensation reaction between o -nitroanilines and alcohols catalyzed by an iron-sulfur system

Unbalanced redox condensation reaction between o-nitroanilines and alcohols, leading to benzimidazole and quinoxaline heterocycles can be efficiently promoted and catalyzed by sodium sulfide (40 mol%) in combination with iron(III) chloride hexahydrate (1 mol%). Beside the role as a precursor for the iron-sulfur (Fe/S) catalyst formation, hydrated sodium sulfide was shown to be an excellent noncompetitive, multi-electron reducing agent.

Copper-catalyzed, one-pot, three-component synthesis of benzimidazoles by condensation and C-N bond formation

Benzimidazoles were synthesized by the copper-catalyzed, one-pot, three-component reaction of 2-haloanilines, aldehydes, and NaN3. The reaction was optimized when 2-iodo- or 2-bromoanilines (1.0 equiv), aldehydes (1.2 equiv), NaN3 (2.0 equiv), 5 mol% of CuCl, and 5 mol % of TMEDA were reacted in DMSO at 120 °C for 12 h. Good yields resulted, and the reaction showed tolerance toward functional groups such as ester, nitro, and chloro. Aliphatic and heteroaromatic aldehydes also afforded the desired products in moderate to good yields.

Non-metal-mediated: N -oxyl radical (TEMPO)-induced acceptorless dehydrogenation of N-heterocycles via electrocatalysis

The development of protocols for direct catalytic acceptorless dehydrogenation of N-heterocycles with metal-free catalysts holds the key to difficulties in green and sustainable chemistry. Herein, an N-oxyl radical (TEMPO) acting as an oxidant in combination with electrochemistry is used as a synthesis system under neutral conditions to produce N-heterocycles such as benzimidazole and quinazolinone. The key feature of this protocol is the utilization of the TEMPO system as an inexpensive and easy to handle radical surrogate that can effectively promote the dehydrogenation reaction. Mechanistic studies also suggest that oxidative TEMPOs redox catalytic cycle participates in the dehydrogenation of 2,3-dihydro heteroarenes. This journal is

A heterogeneous catalytic strategy for facile production of benzimidazoles and quinoxalines from primary amines using the Al-MCM-41 catalyst

This study reports a straightforward heterogeneous catalytic (Al-MCM-41) approach to synthesize nitrogen heterocycle moieties from primary amines under solvent-free conditions. The Al-MCM-41 catalyst was prepared using a hydrothermal method and characterized by various analytical techniques. The probability and limitations of the catalytic methodology were presented with various substrates. The catalytic method grants an attractive route to a wide variety of benzimidazole and quinoxaline moieties with good to excellent yields. The gram scale reaction and reusability (up to five cycles) of the Al-MCM-41 catalyst would greatly benefit industrial applications. This journal is

A one-step synthesis of substituted benzo- and pyridine-fused 1H-imidazoles

Substituted benzimidazoles and pyrimidazoles are an important group of heterocyclic aromatic organic compounds in the field of medicinal chemistry. A one-step microwave accelerated synthesis of substituted benzo- and pyridine-fused 1H-imidazoles has been described. Mechanistically, the reaction proceeds by reacting substituted 2-fluoronitrobenzene and substituted arylamine through the formation of N-hydroxy intermediate, which at higher temperature cleaves to afford the desired product. This approach achieved reductions in reaction times, higher yields, cleaner reactions than the previously described synthetic processes.

Heteroaromatic Inhibitors of the Astacin Proteinases Meprin α, Meprin β and Ovastacin Discovered by a Scaffold-Hopping Approach

Astacin metalloproteinases, in particular meprins α and β, as well as ovastacin, are emerging drug targets. Drug-discovery efforts have led to the development of the first potent and selective inhibitors in the last few years. However, the most recent compounds are based on a highly flexible tertiary amine scaffold that could cause metabolic liabilities or decreased potency due to the entropic penalty upon binding to the target. Thus, the aim of this study was to discover novel conformationally constrained scaffolds as starting points for further inhibitor optimization. Shifting from flexible tertiary amines to rigid heteroaromatic cores resulted in a boost in inhibitory activity. Moreover, some compounds already exhibited higher activity against individual astacin proteinases compared to recently reported inhibitors and also a favorable off-target selectivity profile, thus qualifying them as very suitable chemical probes for target validation.

Oxidative Cyclization Approach to Benzimidazole Libraries

An efficient approach to the parallel synthesis of benzimidazoles from anilines is described. Library approaches to vary the N1 and C2 vectors of benzimidazoles are well established; however, C4-C7 variation has traditionally relied on 1,2-dianiline build

HETEROAROMATIC INHIBITORS OF ASTACIN PROTEINASES

The present invention relates to novel hydroxamic acid derivatives useful as inhibitors of astacin metalloproteinases, in particular procollagen C-proteinase (PCP) enzymes, meprins, ovastacin and/or nematode astacins; more particularly human or mammalian