79762-54-2

Basic information

• Product Name: 6-Bromoindazole
• Synonyms: 6-BROMOINDAZOLE;1H-Indazole, 6-bromo-;6-Bromo-1H-indazole;6-Bromo-1H-indazole 95%;IFLAB-BB F2108-0126;6-BROMO-1H-INDAZOLE
• CAS NO: 79762-54-2
• Molecular Formula: C₇H₅BrN₂
• Molecular Weight: 197.03
• EINECS: 1312995-182-4
• Product Categories: pharmacetical;Indazole;CHIRAL CHEMICALS;Fused Ring Systems;Halides;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building BlocksHeterocyclic Building Blocks;Indazoles;New Products for Chemical Synthesis;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 79762-54-2.mol

Chemical Properties

• Melting Point: 180-182
• Boiling Point: 333.821 °C at 760 mmHg
• Flash Point: 155.69 °C
• Appearance: /
• Density: 1.771 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 12.78±0.40(Predicted)
• CAS DataBase Reference: 6-Bromoindazole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromoindazole(79762-54-2)
• EPA Substance Registry System: 6-Bromoindazole(79762-54-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-41
• Safety Statements: 26-36/37-39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 79762-54-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Bromoindazole is used as an inhibitor of DNA gyrase B for its antibacterial activity. It targets the enzyme DNA gyrase B, which is essential for bacterial DNA replication, transcription, repair, and recombination. By inhibiting this enzyme, 6-Bromoindazole can effectively disrupt the bacterial cell's ability to replicate its DNA, leading to the inhibition of bacterial growth and potentially killing the bacteria.
Furthermore, 6-Bromoindazole is being studied for its potential use in treating bacterial infections caused by antibiotic-resistant strains. Its unique mechanism of action and ability to target DNA gyrase B make it a promising candidate for the development of new antibiotics to combat drug-resistant bacteria.
In addition to its antibacterial properties, 6-Bromoindazole is also being investigated for its potential applications in other areas of pharmaceutical research. Its ability to modulate various biological processes and interact with different molecular targets makes it a versatile compound with potential applications in various therapeutic areas, such as anti-inflammatory, antifungal, and anticancer treatments.
Overall, 6-Bromoindazole is a promising indazole derivative with a wide range of potential applications in the pharmaceutical industry, particularly in the development of new antibiotics to combat antibiotic-resistant bacteria and the exploration of its potential in other therapeutic areas.

Upstream product

• 39478-78-9 5-bromo-2-methylaniline 
• 57848-46-1 4-bromo-2-fluorobenzaldehyde 
• 6967-12-0 6-amino-1H-indazole 
• 12775-96-1 copper 
• 651780-33-5 1-(6-bromo-1H-indazol-1-yl)ethanone 
• 93777-26-5 5-bromo-2-fluorobenzaldehyde 
• 593-56-6 N-methoxylamine hydrochloride 

Downstream Products

• 885521-88-0 6-bromo-3-iodo-1H-indazole 
• 861905-87-5 6-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indazole 
• 937046-99-6 2-benzyl-6-bromoindazole 
• 937049-47-3 6-bromo-2-(2-fluorobenzyl)-2H-indazol-3-amine 
• 937049-58-6 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 
• 1049651-40-2 1-(4-methoxybenzyl)-6-bromo-1H-indazole 
• 1158680-88-6 6-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole 
• 894808-02-7 6-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole 
• 651780-33-5 1-(6-bromo-1H-indazol-1-yl)ethanone 
• 669050-69-5 1H-indazole-6-carboxyaldehyde 
• 1201645-12-6 2-(4-((6-(1H-indazol-6-yl)-3-nitroquinolin-4-yl)methyl)phenyl)-2-methylpropanenitrile 
• 1204400-68-9 C₁₅H₁₇N₃O₂ 
• 1248590-87-5 N-(pyridin-2-yl)-1H-indazol-6-amine 
• 1248590-80-8 4-(4-chlorophenyl)-1-(1H-indazol-6-yl)piperidin-4-ol 

Relevant articles and documents

Compound with AMPK agonistic activity and preparation and application of prodrug thereof

The invention relates to a compound with AMPK agonistic activity and a prodrug thereof, and as well as a preparation method and medical application of a prodrug thereof. The compound has the structure shown in the formula (I), and the prodrug of the compound has the structure shown in the formula (II), wherein each group and the substituent are as defined in the specification. The invention discloses a preparation method of the compound and application of the compound in prevention and treatment AMPK related diseases, and the AMPK related diseases include, but are not limited to, energy metabolism abnormality related diseases. Neurodegenerative diseases and inflammation-related diseases and the like.

Design, synthesis and biological evaluation of novel 2-(4-(1H-indazol-6-yl)-1H-pyrazol-1-yl)acetamide derivatives as potent VEGFR-2 inhibitors

Vascular endothelial growth factor-2 (VEGFR-2) plays a pivotal role in tumor angiogenesis. Herein, a library of novel 2-(4-(1H-indazol-6-yl)-1H-pyrazol -1-yl)acetamide derivatives were designed and synthesized as VEGFR-2 inhibitors based on scaffold hopping strategy. These compounds exhibited the excellent inhibitory in both VEGFR-2 and tumor cells proliferation. Especially, compound W13 possessed potent VEGFR-2 inhibition with IC50 = 1.6 nM and anti-proliferation against HGC-27 tumor cells with IC50 = 0.36 ± 0.11 μM, as well as less toxicity against normal GES-1 cells with IC50 = 187.46 ± 10.13 μM. Moreover, W13 obviously inhibited colony formation, migration and invasion of HGC-27 cells by adjusting the expression of MMP-9 and E-cadherin, and induced HGC-27 cells apoptosis by increasing ROS production and regulating the expression of apoptotic proteins. Furthermore, W13 blocked the PI3K-Akt-mTOR signaling pathway in HGC-27 cells. In addition, anti-angiogenesis of W13 was proved by inhibiting tube formation and the expression of p-VEGFR-2 in HUVEC cells. All the results demonstrated that W13 could be developing as a promising anticancer agent for gastric cancer therapy.

TYK2 INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of TYK2, and the treatment of TYK2-mediated disorders.

Micromolecular reversible BTK inhibitor for treating rheumatoid arthritis

The invention relates to a micromolecular reversible BTK inhibitor for treating rheumatoid arthritis, and specifically provides a compound. The compound is the compound as shown in a formula I, or a stereisomer, a geometrical isomer and a tautomer thereof, nitric oxide, aquo-complex, a solvate, a metabolite and pharmaceutically acceptable salts and prodrugs. The inventor finds that polysubstitutedquinolone compound or derivate thereof as shown in formula I can be used as the BTK inhibitor and is high in activity during treating rheumatoid arthritis.

Discovery of 4-Aminoquinoline-3-carboxamide derivatives as potent reversible Bruton's tyrosine kinase inhibitors for the treatment of rheumatoid arthritis

A structure-hopping strategy was applied to discover a series of novel 4-aminoquinoline-3-carboxamide derivatives as potent, reversible BTK inhibitors. Compared to the previously described cinnoline scaffold compounds, the 4-aminoquinoline analogues showed significantly improved drug-like properties, especially in their aqueous solubility. The most potent compound, 25, displayed a stronger inhibitory effect on both BTKWT (IC50 = 5.3 nM) and BTKC481S (IC50 = 39 nM). In a rodent collagen-induced arthritis model, compound 25 efficiently reduced paw swelling without a loss in body weight. On the basis of potency, drug-like properties, stability, and noncovalent mode of inhibition, our representative inhibitors could have a promising profile to be treatments for a wide range of autoimmune diseases.

Discovery of 5-Azaindazole (GNE-955) as a Potent Pan-Pim Inhibitor with Optimized Bioavailability

Pim kinases have been identified as promising therapeutic targets for hematologic-oncology indications, including multiple myeloma and certain leukemia. Here, we describe our continued efforts in optimizing a lead series by improving bioavailability while maintaining high inhibitory potency against all three Pim kinase isoforms. The discovery of extensive intestinal metabolism and major metabolites helped refine our design strategy, and we observed that optimizing the pharmacokinetic properties first and potency second was a more successful approach than the reverse. In the resulting work, novel analogs such as 20 (GNE-955) were discovered bearing 5-azaindazole core with noncanonical hydrogen bonding to the hinge.

Indazole derivative, composition and uses thereof

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AZA SPIRO ALKANE DERIVATIVES AS INHIBITORS OF METALLPROTEASES

The present invention provides a compound of Formula (I) or Formula (II): enantiomer, diastereomer, prodrug, solvate, metabolite, or pharmaceutically acceptable salt thereof, wherein constituent variables are provided herein. The compounds of Formula (I) and (II) are modulators of metalloproteases and are useful in treating diseases associated with metalloprotease activity such as arthritis, cancer, cardiovascular disorders, skin disorders, inflammation and allergic conditions.

INHIBITORS OF FATTY ACID AMIDE HYDROLASE

The present invention provides compounds, and pharmaceutically acceptable compositions thereof, encompassed by any of formulae (I), (II), (III), (IV), (V), or (VI), or subgenera thereof. The present invention also provides methods for treating an FAAH mediated disease, disorder or condition by administering a therapeutically effective amount of a compound or composition comprising a compound of any of formulae (I), (II), (III), (IV), (V), or (VI), or subgenera thereof, to a patient in need thereof. Additionally, the present invention provides methods for inhibiting FAAH by administering a therapeutically effective amount of a compound or composition comprising a compound of any of formulae (I), (II), (III), (IV), (V), or (VI), or subgenera thereof, to a patient in need thereof.

A novel series of indazole-/indole-based glucagon receptor antagonists

A novel, potent series of glucagon receptor antagonists (GRAs) was discovered. These indazole- and indole-based compounds were designed on an earlier pyrazole-based GRA lead MK-0893. Structure-activity relationship (SAR) studies were focused on the C3 and C6 positions of the indazole core, as well as the benzylic position on the N-1 of indazole. Multiple potent GRAs were identified with excellent in vitro profiles and good pharmacokinetics in rat. Among them, GRA 16d was found to be orally active in blunting glucagon induced glucose excursion in an acute glucagon challenge model in glucagon receptor humanized (hGCGR) mice at 1, 3 and 10 mg/kg (mpk), and significantly lowered acute glucose levels in hGCGR ob/ob mice at 3 mpk dose.