30384-96-4

Usage

Uses

Used in Pharmaceutical Industry:
6-BROMOIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure and reactivity enable the development of novel drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 6-BROMOIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE serves as an essential building block for the synthesis of agrochemicals, contributing to the development of innovative and effective products for crop protection and pest control.
Used in Organic Material Synthesis:
6-BROMOIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE is utilized as a versatile intermediate in the synthesis of organic materials, such as dyes, pigments, and functional polymers, due to its ability to participate in various organic transformations.
Used in Medicinal Chemistry Research:
As a widely studied chemical compound, 6-BROMOIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE plays a significant role in medicinal chemistry research, where it is employed for the exploration of new chemical entities and the investigation of their biological activities.
Used in Drug Discovery:
6-BROMOIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE has potential applications in drug discovery, where it can be used to design and optimize novel drug candidates with improved pharmacological properties and therapeutic potential.

InChI:InChI=1/C8H5BrN2O/c9-6-1-2-8-10-3-7(5-12)11(8)4-6/h1-5H

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 6188-23-4 6-bromoimidazo[1,2-a]pyridine 
• 107-20-0 2-chloroethanal 
• 138888-98-9 N’-(5-bromopyridin-2-yl)-N,N-dimethylformimidamide 
• 1072-97-5 5-bromo-2-pyridylamine 
• 2065-75-0 2-Bromo-malonaldehyde 

Downstream Products

• 945619-40-9 N'-((6-bromoimidazo[1,2-a]pyridin-3-yl)methylene)-2-methyl-5-nitrobenzenesulfonohydrazide 
• 372196-67-3 [2-methyl-5-nitro-1-benzenesulfonic acid 2-[(6-bromoimidazo[1,2-a]pyridin-3-yl)methylene]-1-methylhydrazide] 
• 1207561-85-0 6-bromo-3-[(4-methoxyphenyl)methyl]imidazo[1,2-a]pyridine 

Relevant academic research and scientific papers

Preparation method of 6-bromoimidazo[1.2-a]pyridine-3-formaldehyde

The invention relates to a preparation method of 6-bromoimidazo[1.2-a]pyridine-3-formaldehyde. The method comprises the following steps: 1, adding 2-amino-5-bromopyridine and N,N-dimethylformamide dimethyl acetal into a reactor to react, and stirring to react to obtain an N,N-dimethyl-N'-2-(5-bromo-pyridine)yl-formamidine intermediate; 2, adding the N,N-dimethyl-N'-2-(5-bromo-pyridine)yl-formamidine intermediate obtained in the step 1 into a solvent, adding chloroacetaldehyde, and carrying out a reaction to obtain a solid mixture; 3, dissolving the solid mixture in ethyl acetate, washing withwater and saturated edible salt water, drying with anhydrous sodium sulfate, filtering, and removing ethyl acetate to obtain a 6-bromoimidazo[1.2-a]pyridine-3-formaldehyde crude product; and 4, recrystallizing the 6-bromoimidazo[1.2-a]pyridine-3-formaldehyde crude product, and filtering to obtain a 6-bromoimidazo[1.2-a]pyridine-3-formaldehyde pure product. According to the preparation method, thereaction raw materials are easy to obtain, the price is reasonable, the reaction conditions are mild, operation is easy, aftertreatment is simple, and the product is stable in quality and high in purity.

Copper- A nd DMF-mediated switchable oxidative C-H cyanation and formylation of imidazo[1,2-: A] pyridines using ammonium iodide

The cyanation and formylation of imidazo[1,2-a]pyridines were developed under copper-mediated oxidative conditions using ammonium iodide and DMF as a nontoxic combined cyano-group source and DMF as a formylation reagent. Mechanistic studies indicate that the cyanation of imidazo[1,2-a]pyridines proceeds through a two-step sequence: Initial iodination and then cyanation. The cyanation has a broad substrate scope and high functional group tolerance, and can be safely conducted on a gram scale. A novel copper-mediated formylation using the widely available DMF as the formylation reagent and environmentally friendly molecular oxygen as the oxidant has also been developed. This protocol also provided a convenient approach for the synthesis of clinically used saripidem. This journal is

Microwave-assisted synthesis of 3-formyl substituted imidazo[1,2-a]pyridines

An efficient, metal-free method for the synthesis of 3-formyl imidazo[1,2-a]pyridines is reported. The method utilises commercially available substrates and features a broad substrate scope. The intermediate enamine was isolated and a plausible reaction mechanism proposed.

An Unusual Intramolecular Halogen Bond Guides Conformational Selection

PIK-75 is a phosphoinositide-3-kinase (PI3K) α-isoform-selective inhibitor with high potency. Although published structure–activity relationship data show the importance of the NO2 and the Br substituents in PIK-75, none of the published studies could correctly determine the underlying reason for their importance. In this publication, we report the first X-ray crystal structure of PIK-75 in complex with the kinase GSK-3β. The structure shows an unusual U-shaped conformation of PIK-75 within the active site of GSK-3β that is likely stabilized by an atypical intramolecular Br???NO2 halogen bond. NMR and MD simulations show that this conformation presumably also exists in solution and leads to a binding-competent preorganization of the PIK-75 molecule, thus explaining its high potency. We therefore suggest that the site-specific incorporation of halogen bonds could be generally used to design conformationally restricted bioactive substances with increased potencies.

Identification of the Privileged Position in the Imidazo[1,2-a]pyridine Ring of Phosphonocarboxylates for Development of Rab Geranylgeranyl Transferase (RGGT) Inhibitors

Members of the Rab GTPase family are master regulators of vesicle trafficking. When disregulated, they are associated with a number of pathological states. The inhibition of RGGT, an enzyme responsible for post-translational geranylgeranylation of Rab GTPases represents one way to control the activity of these proteins. Because the number of molecules modulating RGGT is limited, we combined molecular modeling with biological assays to ascertain how modifications of phosphonocarboxylates, the first reported RGGT inhibitors, rationally improve understanding of their structure-activity relationship. We have identified the privileged position in the core scaffold of the imidazo[1,2-a]pyridine ring, which can be modified without compromising compounds' potency. Thus modified compounds are micromolar inhibitors of Rab11A prenylation, simultaneously being inactive against Rap1A/Rap1B modification, with the ability to inhibit proliferation of the HeLa cancer cell line. These findings were rationalized by molecular docking, which recognized interaction of phosphonic and carboxylic groups as decisive in phosphonocarboxylate localization in the RGGT binding site.

Design, synthesis and biological evaluation of acylhydrazone derivatives as PI3K inhibitors

Since the PI3K signaling pathway is the most commonly activated in human cancers, inhibition of PI3K is a promising approach to cancer therapy. In this study, a series of 2-methyl-5-nitrobenzeneacylhydrazones were designed and synthesized. All the new der

IMIDAZOPYRIDINE DERIVATIVES

The present invention relates to compounds of formula (I), wherein Ra, Rb, Rc, Rd, Re and Rf are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases mediated by phosphatidylinositol-3-kinase (PBK), mammalian target of rapamycin (mTOR), Signal transducer and activator of transcription 3 (STAT 3), tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6) or a combination thereof particularly in the treatment of cancer and inflammation.

Synthesis and biological evaluation of sulfonylhydrazone-substituted imidazo[1,2-a]pyridines as novel PI3 kinase p110α inhibitors

We have previously reported the imidazo[1,2-a]pyridine derivative 4 as a novel p110α inhibitor; however, although 4 is a potent inhibitor of p110α enzymatic activity and tumor cell proliferation in vitro, it is unstable in solution and ineffective in vivo