183208-22-2

Basic information

• Product Name: 5-BroMo-1-Methyl-7-azaind...
• Synonyms: 5-BroMo-1-Methyl-7-azaind...;5-BroMo-1-Methyl-7-azaindole;5-broMo-1-Methyl-1H-pyrrolo[2,3-b]pyridine;5-BroMo-1-Methylpyrrolo[2,3-b]pyridine;1H-Pyrrolo[2,3-b]pyridine, 5-bromo-1-methyl-
• CAS NO: 183208-22-2
• Molecular Formula: C₈H₇BrN₂
• Molecular Weight: 211.07
• Mol File: 183208-22-2.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 294.3±20.0 °C(Predicted)
• Appearance: /
• Density: 1.60±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.11±0.30(Predicted)
• CAS DataBase Reference: 5-BroMo-1-Methyl-7-azaind...(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BroMo-1-Methyl-7-azaind...(183208-22-2)
• EPA Substance Registry System: 5-BroMo-1-Methyl-7-azaind...(183208-22-2)

Safety Data

• Hazardous Substances Data: 183208-22-2(Hazardous Substances Data)

Usage

General Description

The chemical "5-Bromo-1-Methyl-7-azaindole" is a specialized chemical compound often used in scientific research, particularly in the field of organic chemistry. 5-BroMo-1-Methyl-7-azaind... is distinguished by its unique structure featuring a bromine atom and a nitrogen atom. It's a type of azaindole, a class of chemical compounds typified by a fused pyrrole and pyridine ring structure, with a nitrogen atom substituted in. 5-BroMo-1-Methyl-7-azaind..., like other azaindoles, has potential use in pharmacological development and biological research, notably as intermediates for the synthesis of different bioactive molecules. Its handling requires safety measures due to its reactivity and potential hazards.

Upstream product

• 905966-34-9 5-bromo-3-(2-(trimethylsilyl)ethynyl)pyridine-2-amine 
• 381233-96-1 2-amino-3-iodo-5-bromopyridine 
• 183208-35-7 5-bromo-1H-pyrrolo[2,3-b]pyridine 
• 183208-32-4 3,3,5-Tribromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one 
• 183208-34-6 5-bromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one 
• 271-63-6 7-Azaindole 
• 74-88-4 methyl iodide 

Downstream Products

• 1220696-34-3 (S)-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine 
• 934568-20-4 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid 

Relevant articles and documents

Characterization of maleimide-based glycogen synthase kinase-3 (GSK-3) inhibitors as stimulators of steroidogenesis

Inhibition of GSK-3β has been well documented to account for the behavioral actions of the mood stabilizer lithium in various animal models of mood disorders. Recent studies have showed that genetic or pharmacological inhibition of GSK-3β resulted in anxiolytic-like and pro-social behavior. In our ongoing efforts to develop GSK-3β inhibitors for the treatment of mood disorders, SAR studies on maleimide-based compounds were undertaken. We present herein for the first time that some of these GSK-3β inhibitors, in particular analogues 1 and 9, were able to stimulate progesterone production in the MA-10 mouse tumor Leydig cell model of steroidogenesis without any significant toxicity. These two compounds were tested in the SmartCube behavioral assay and showed anxiolytic-like signatures following daily dose administration (50 mg/kg, ip) for 13 days. Taken together, these results support the hypothesis that GSK-3β inhibition could influence neuroactive steroid production thereby mediating the modulation of anxiety-like behavior in vivo.

Synthesis of new melatonin analogues from dimers of azaindole and indole by use of Suzuki homocoupling

N-{2-[3′-(2-Acetylaminoethyl)-1H,1′H-[5,5′]biindol-3-yl]- and N-{2-[1′-(2-acetylaminoethyl)-1′H-[5, 5′]biindol-1-yl]ethyl}acetamide (2,3) and their analogues in 7-azaindole series (4,5) were synthesized by palladium catalysed reaction starting from indole or 7-azaindole using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium, as catalyst.

Scaffold-Hopping Strategy on a Series of Proteasome Inhibitors Led to a Preclinical Candidate for the Treatment of Visceral Leishmaniasis

There is an urgent need for new treatments for visceral leishmaniasis (VL), a parasitic infection which impacts heavily large areas of East Africa, Asia, and South America. We previously reported on the discovery of GSK3494245/DDD01305143 (1) as a preclinical candidate for VL and, herein, we report on the medicinal chemistry program that led to its identification. A hit from a phenotypic screen was optimized to give a compound with in vivo efficacy, which was hampered by poor solubility and genotoxicity. The work on the original scaffold failed to lead to developable compounds, so an extensive scaffold-hopping exercise involving medicinal chemistry design, in silico profiling, and subsequent synthesis was utilized, leading to the preclinical candidate. The compound was shown to act via proteasome inhibition, and we report on the modeling of different scaffolds into a cryo-EM structure and the impact this has on our understanding of the series' structure-activity relationships.

Synthesis and Structure-Activity Relationships of 3,5-Disubstituted-pyrrolo[2,3- b]pyridines as Inhibitors of Adaptor-Associated Kinase 1 with Antiviral Activity

There are currently no approved drugs for the treatment of emerging viral infections, such as dengue and Ebola. Adaptor-associated kinase 1 (AAK1) is a cellular serine-threonine protein kinase that functions as a key regulator of the clathrin-associated host adaptor proteins and regulates the intracellular trafficking of multiple unrelated RNA viruses. Moreover, AAK1 is overexpressed specifically in dengue virus-infected but not bystander cells. Because AAK1 is a promising antiviral drug target, we have embarked on an optimization campaign of a previously identified 7-azaindole analogue, yielding novel pyrrolo[2,3-b]pyridines with high AAK1 affinity. The optimized compounds demonstrate improved activity against dengue virus both in vitro and in human primary dendritic cells and the unrelated Ebola virus. These findings demonstrate that targeting cellular AAK1 may represent a promising broad-spectrum antiviral strategy.