148038-83-9

Basic information

• Product Name: 2H-Imidazo[4,5-b]pyridin-2-one,6-bromo-1,3-dihydro-
• Synonyms: 6-Bromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;6-Bromo-1,3-dihydroimidazo[4,5-b]pyridin-2-one
• CAS NO: 148038-83-9
• Molecular Formula: C₆H₄BrN₃O
• Molecular Weight: 214.0195
• Mol File: 148038-83-9.mol

Chemical Properties

• Melting Point: >350°
• Boiling Point: 189.4 °C at 760 mmHg
• Flash Point: 68.4 °C
• Appearance: /
• Density: 1.837 g/cm³
• Vapor Pressure: 0.57mmHg at 25°C
• Refractive Index: 1.636
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.36±0.20(Predicted)
• CAS DataBase Reference: 2H-Imidazo[4,5-b]pyridin-2-one,6-bromo-1,3-dihydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Imidazo[4,5-b]pyridin-2-one,6-bromo-1,3-dihydro-(148038-83-9)
• EPA Substance Registry System: 2H-Imidazo[4,5-b]pyridin-2-one,6-bromo-1,3-dihydro-(148038-83-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 148038-83-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
2H-Imidazo[4,5-b]pyridin-2-one,6-bromo-1,3-dihydrois used as a chemical intermediate for the synthesis of various bioactive compounds. Its unique structure allows for the development of new drugs targeting specific biological pathways, making it a valuable asset in the pharmaceutical industry.
Used in Drug Development:
As a starting material, 2H-Imidazo[4,5-b]pyridin-2-one,6-bromo-1,3-dihydrois utilized in the development of new drugs with potential pharmacological properties. Its structure enables researchers to explore its impact on biological systems and create innovative therapeutic agents.
Used in Biological Pathway Targeting:
2H-Imidazo[4,5-b]pyridin-2-one,6-bromo-1,3-dihydrois employed as a building block for the creation of compounds that target specific biological pathways. This allows for the development of drugs with precise mechanisms of action, potentially leading to more effective treatments for various diseases.
Used in Biological System Studies:
2H-Imidazo[4,5-b]pyridin-2-one,6-bromo-1,3-dihydrois also used in the study of its impact on biological systems, providing insights into its potential pharmacological properties and applications. Understanding its interactions with biological targets can guide the development of more effective and targeted therapeutic agents.

InChI:InChI=1/C6H4BrN3O/c7-3-1-4-5(8-2-3)10-6(11)9-4/h1-2H,(H2,8,9,10,11)

Upstream product

• 38875-53-5 5-bromo-pyridine-2,3-diamine 
• 530-62-1 1,1'-carbonyldiimidazole 
• 74124-79-1 di(succinimido) carbonate 
• 273-21-2 3H-imidazo[4,5-b]pyridine 
• 57-13-6 urea 

Relevant articles and documents

Optimization of 5-substituted thiazolyl ureas and 6-substituted imidazopyridines as potential HIV-1 latency reversing agents

A persistent latent reservoir of virus in CD4+ T cells is a major barrier to cure HIV. Activating viral transcription in latently infected cells using small molecules is one strategy being explored to eliminate latency. We previously described the use of a FlpIn.FM HEK293 cellular assay to identify and then optimize the 2-acylaminothiazole class to exhibit modest activation of HIV gene expression. Here, we implement two strategies to further improve the activation of viral gene expression and physicochemical properties of this class. Firstly, we explored rigidification of the central oxy-carbon linker with a variety of saturated heterocycles, and secondly, investigated bioisosteric replacement of the 2-acylaminothiazole moiety. The optimization process afforded lead compounds (74 and 91) from the 2-piperazinyl thiazolyl urea and the imidazopyridine class. The lead compounds from each class demonstrate potent activation of HIV gene expression in the FlpIn.FM HEK293 cellular assay (both with LTR EC50s of 80 nM) and in the Jurkat Latency 10.6 cell model (LTR EC50 220 and 320 nM respectively), but consequently activate gene expression non-specifically in the FlpIn.FM HEK293 cellular assay (CMV EC50 70 and 270 nM respectively) manifesting in cellular cytotoxicity. The lead compounds have potential for further development as novel latency reversing agents.

Design, Synthesis, and Preclinical Evaluation of 3-Methyl-6-(5-thiophenyl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-ones as Selective GluN2B Negative Allosteric Modulators for the Treatment of Mood Disorders

Selective inhibitors of the GluN2B subunit of N-methyl-d-aspartate receptors in the ionotropic glutamate receptor superfamily have been targeted for the treatment of mood disorders. We sought to identify structurally novel, brain penetrant, GluN2B-selective inhibitors suitable for evaluation in a clinical setting in patients with major depressive disorder. We identified a new class of negative allosteric modulators of GluN2B that contain a 1,3-dihydro-imidazo[4,5-b]pyridin-2-one core. This series of compounds had poor solubility properties and poor permeability, which was addressed utilizing two approaches. First, a series of structural modifications was conducted which included replacing hydrogen bond donor groups. Second, enabling formulation development was undertaken in which a stable nanosuspension was identified for lead compound 12. Compound 12 was found to have robust target engagement in rat with an ED70 of 1.4 mg/kg. The nanosuspension enabled sufficient margins in preclinical toleration studies to nominate 12 for progression into advanced good laboratory practice studies.

SUBSTITUTED 1H-IMIDAZO[4,5-B]PYRIDIN-2(3H)-ONES AND THEIR USE AS GLUN2B RECEPTOR MODULATORS

Substituted 1 H-imidazo[4,5-b]pyridin-2(3H)-ones as NR2B receptor ligands. Such compounds may be used in NR2B receptor modulation and in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by NR2B receptor activity.

HETEROCYCLIC COMPOUNDS AS INHIBITORS OF FATTY ACID BIOSYSNTHESIS FOR BACTERIAL INFECTIONS

The present invention relates to novel heterocyclic compounds which specifically inhibit bacterial FabI and can be used for the treatment of Staphylococcal infections.

HETEROCYCLIC COMPOUNDS AS INHIBITORS OF FATTY ACID BIOSYNTHESIS FOR BACTERIAL INFECTIONS

The present invention relates to novel heterocyclic compounds which specifically inhibit bacterial Fab I and can be used for the treatment of Staphylococcal infections.

QUINAZOLINES AS POTASSIUM ION CHANNEL INHIBITORS

A compound of formula (I) wherein A, X, Y, Z, R1 and R24 are described herein. The compounds are useful as inhibitors of potassium channel function and in the treatment and prevention of arrhythmia, IKur-associated disorders, and other disorders mediated by ion channel function.

BICYCLIC HETEROARYL KINASE INHIBITORS AND METHODS OF USE

Provided are compounds having an inhibitory effect on kinases including Mixed Lineage Kinases. Also provided are pharmaceutical compositions, methods of preparing the compounds, synthetic intermediates, and methods of using the compounds, independently or in combination with other therapeutic agents, for treating diseases and conditions that are affected by Mixed Lineage Kinase inhibition. Also provided are methods of treatment of neuropsychiatric disorders that comprise the inhibition of Mixed Lineage Kinases.

1,4-BENZODIAZEPINONE COMPOUNDS AND THEIR USE IN TREATING CANCER

The invention provides a family of 1,4-benzodiazepinone compounds and methods for their use as therapeutic agents in treating cancer. Pharmaceutical compositions and methods of making the 1,4-benzodiazepinone compounds are provided.

BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS VANILLOID RECEPTOR LIGANDS

Compounds of formula (I) are useful in the treatment of vanilloid-receptor-meditated diseases, such as inflammatory or neuropathic pain and diseases involving sensory nerve function such as asthma, rheumatoid arthritis, osteoarthritis, inflammatory bowel disorders, urinary incontinence, migraine and psoriasis.