5-Bromo-7-azaindole CAS 183208-35-7

1. Core intermediates in the synthesis of anti-tumor drugs
The most important and core industrial use is as a synthetic intermediate for BRAF inhibitor Virofenib. Velocitinib was jointly developed by Roche and Plexxikon in the United States. It was approved by the FDA in 2011 and marketed under the brand name Zelboraf. It was the first approved targeted drug for BRAF V600E mutant melanoma, completely changing the treatment landscape for advanced melanoma. In the synthetic route of Virofenib, its bromine atom is substituted with various aryl, heteroaromatic, or amino groups through palladium catalyzed cross coupling reactions such as Suzuki coupling, Buchwald Hartwig amination, or Sonogashira coupling, thereby constructing the key 7-azaindole aryl linkage structure in Virofenib molecules.

In addition to Virofenib, it is also an important synthetic intermediate for the BCL-2 selective inhibitor ABT-199, also known as Venetoclax. Venetoclax, jointly developed by AbbVie and Genentech, was approved by the FDA in 2016 under the trade name Venclexta. It is the first BCL-2 protein inhibitor used to treat chronic lymphocytic leukemia and acute myeloid leukemia. In the synthesis of ABT-199, the key pharmacophore is also introduced through the coupling reaction of bromine atoms, which is one of the starting blocks for the construction of the entire molecular skeleton. In addition, it has been widely used in the synthesis of new drug candidates such as PP121 cell signaling pathway inhibitors and LKB1 or AAK1 inhibitors.

2. A universal block for protein kinase inhibitor drugs
Azaindole, also known as 7-azaindole, is a recognized important drug scaffold in the field of medicinal chemistry, also known as a privileged scaffold. Its structure is highly similar to purine bases and can simulate the binding mode between ATP and kinases, making it widely used in the design of protein kinase inhibitors. 5-bromo-7-azindole, as a brominated derivative of Azaindole, has its 5th bromine atom as an ideal site for structural diversity modification. By introducing different substituents at this site, the binding affinity and selectivity of the molecule to the kinase active pocket can be systematically regulated.

Research has confirmed that derivatives synthesized from it exhibit significant inhibitory activity against multiple targets. In the field of neuroscience, its derivatives have been developed as positive allosteric modulators of α 7-nicotinic acetylcholine receptors, as detailed in the 2021 European Journal of Medicinal Chemistry. In the field of anti infection, its derivatives have broad-spectrum inhibitory activity against various tyrosine kinases and serine or threonine kinases, which has been validated by multiple high-throughput screenings. In the field of antiviral, Xiamen University's patent published in 2021 reported that its derivatives have anti coronavirus activity. Therefore, it is hailed by medicinal chemists as the master key to the development of protein kinase inhibitor drugs.

3. Biochemical reagents for life science research
5-Bromo-7-azindole, as a biochemical reagent, has a wide and in-depth application in basic research of life sciences. In the study of cellular signaling pathways, it is used as a small molecule probe to investigate kinase signaling cascades. Its nitrogen indole skeleton can competitively bind to ATP binding sites, revealing key nodes in signal transduction. In protein structural biology, it is used as a co crystallization ligand to decipher the three-dimensional structure of kinases, and its bromine atom can be used for heavy atom phase analysis, helping researchers obtain high-resolution protein crystal structures.

In chemical biology, researchers utilize the property that bromine atoms can be converted into click chemical functional groups such as azides and alkynes to synthesize active probes for labeling and tracking the dynamic changes of target proteins within cells. In high-throughput drug screening, compound libraries based on 5-bromo-7-azindole have become the standard tool for drug lead compound discovery by major pharmaceutical companies and academic institutions due to their efficient coupling reactions and suitability for combinatorial chemistry. Its derivatives have been proven to inhibit the activity of various proteases, thus having potential biological and medicinal value, and are widely used in medical research.

5. Signal regulatory factors in plant disease resistance research
This is a little-known but highly academically valuable use of the substance. Research has shown that the signaling pathway of 5-bromo-7-azaindole can control plant growth and insect resistance responses mediated by the inducer Harpin protein. Harpin protein is a type of elastin secreted by plant pathogenic bacteria, which can trigger hypersensitivity reactions and systemic acquired resistance in plants.

In the process of plant disease resistance, it plays a key regulatory role at critical nodes.

It can respond to both jasmonic and ethylene signals, and is a key factor in the synergistic effect between jasmonic and ethylene. In terms of pathogen resistance, it regulates plant resistance to saprophytic pathogens and has a positive regulatory effect on plant bacterial resistance. In terms of growth and development, it synergistically regulates plant growth and development as well as resistance to pathogens with jasmonic acid. This discovery provides a novel molecular target for the development of new plant immune activators, which has significant agricultural application prospects and is expected to reduce pesticide use and promote the development of green agriculture.

6. Pesticide Carrier and Hydrogel Materials
It has shown remarkable application prospects in the fields of pesticide slow-release and biomaterials. In terms of pesticide slow release, the carrier based on it has good pesticide slow release performance, can adjust the density of hydrogel network, control the thermal movement and surface exchange rate of pesticide molecules, so as to achieve long-term and stable release of pesticides. In the aspect of antibacterial hydrogel, researchers have prepared intelligent hydrogel with antibacterial and angiogenesis capabilities by cross-linking multi arm thioalkylated polyethylene glycol and 5-bromo-7-azaindole, and loading ferramine.

It shows great potential in the field of wound dressing by using the dynamic characteristics of silver sulfur coordination bonds and the antibacterial effect of silver ions. In the aspect of hemostatic gel, after the introduction of this product, the material can maintain the sealing ability of the hemostatic agent to the humid environment and sports tissues, greatly accelerate the polymerization speed, effectively avoid the material from being damaged by blood before forming the adhesive gel, and provide a new material choice for emergency medicine.