50593-30-1

Usage

Uses

Used in Pharmaceutical Industry:
6-AMINO-2-METHYL-2H-INDAZOLE is used as a chemical intermediate for the synthesis of new drugs, leveraging its unique structure to target specific biological pathways and mechanisms. Its potential applications include the development of therapeutic agents for a range of medical conditions, driven by its capacity to interact with various molecular targets in the human body.
Given the provided materials, specific applications or industries for 6-AMINO-2-METHYL-2H-INDAZOLE beyond the pharmaceutical industry are not detailed. However, its role as a chemical intermediate suggests that it could be instrumental in the discovery and creation of novel pharmaceutical compounds, which may subsequently be applied across different therapeutic areas such as oncology, neurology, or cardiology, depending on the drug development outcomes. Further research would be required to identify and validate these applications.

InChI:InChI=1/C8H9N3/c1-11-5-6-2-3-7(9)4-8(6)10-11/h2-5H,9H2,1H3

Upstream product

• 6850-22-2 2-methyl-6-nitro-2H-indazole 
• 77-78-1 dimethyl sulfate 
• 7597-18-4 6-nitroindazole 
• 74-88-4 methyl iodide 
• 590417-95-1 6-bromo-2-methyl-2H-indazole 
• 99-55-8 2-methyl-5-nitroaniline 
• 95-53-4 o-toluidine 

Downstream Products

• 112635-17-3 2-Methyl-7,8-diphenyl-2,6-dihydro-pyrrolo[2,3-g]indazole 
• 132283-43-3 2-(2-Methyl-2H-indazol-6-ylamino)-benzoic acid 
• 52470-67-4 2-methyl-6-hydroxyindazole 
• 1620059-35-9 C₁₅H₁₄ClN₅ 
• 1620059-17-7 5-[[4-[N-(2-methyl-2H-indazol-6-yl)-N-methylamino]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl]amino]-2-methyl-benzenesulfonamide 
• 1311986-79-4 N²-(3,5-dimethylphenyl)-N⁴-methyl-N⁴-(2-methyl-2H-indazol-6-yl)pyrimidine-2,4-diamine 
• 1311986-81-8 N⁴-methyl-N⁴-(2-methyl-2H-indazol-6-yl)-N²-(4-(trifluoromethoxy)phenyl)pyrimidine-2,4-diamine 
• 1311986-75-0 N²-(3-methoxyphenyl)-N⁴-methyl-N⁴-(2-methyl-2H-indazol-6-yl)pyrimidine-2,4-diamine 
• 1311986-77-2 N²-(3-chlorophenyl)-N⁴-methyl-N⁴-(2-methyl-2H-indazol-6-yl)pyrimidine-2,4-diamine 
• 1311986-73-8 N²-(3-fluorophenyl)-N⁴-methyl-N⁴-(2-methyl-2H-indazol-6-yl)pyrimidine-2,4-diamine 
• 1064152-85-7 2-Amino-N-(2-methyl-2H-indazol-6-yl)-benzamide 
• 474799-57-0 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(2-methyl-2H-indazol-6-yl)-benzamide 
• 128056-51-9 2-(4-Chloro-phenyl)-9-methyl-5,9-dihydro-2H-1,2,5,9,10-pentaaza-dicyclopenta[a,h]naphthalen-3-one 

Relevant academic research and scientific papers

Design, synthesis and bioevaluation of novel 6-substituted aminoindazole derivatives as anticancer agents

In the present study, a series of 6-substituted aminoindazole derivatives were designed, synthesized, and evaluated for bio-activities. The compounds were initially designed as indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors based on the structural feature of five IDO1 inhibitors, which are currently on clinical trials, and the important anticancer activity of the indazole scaffold. One of them, compound N-(4-fluorobenzyl)-1,3-dimethyl-1H-indazol-6-amine (36), exhibited a potent anti-proliferative activity with an IC50 value of 0.4 ± 0.3 μM in human colorectal cancer cells (HCT116). This compound also remarkably suppressed the IDO1 protein expression. In the cell-cycle studies, the suppressive activity of compound 36 in HCT116 cells was related to the G2/M cell cycle arrest. Altogether, the current findings demonstrate that compound 36 would be promising for further development as a potential anticancer agent.

HEPARAN SULFATE BIOSYNTHESIS INHIBITORS FOR THE TREATMENT OF DISEASES

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions in need of inhibition of heparan sulfate biosynthesis.

SUBSTITUTED HETEROARYL COMPOUNDS AND METHODS OF USE

The present invention provides novel heteroaryl compounds, pharmaceutical acceptable salts and formulations thereof useful in preventing, managing, treating or lessening the severity of a protein kinase-mediated disease. The invention also provides pharma

Substituted heteroaryl compound, and composition and use thereof

The invention provides a substituted heteroaryl compound, and a composition and a use thereof. The compound is a compound represented by formula (I), or a stereoisomer, a tautomer, a nitrogen oxide, a solvate, a metabolite, a pharmaceutically acceptable s

Synthesis and biological evaluation of novel pazopanib derivatives as antitumor agents

A series of novel pazopanib derivatives, 7a-m, were designed and synthesized by modification of terminal benzene and indazole rings in pazopanib. The structures of all the synthesized compounds were confirmed by 1H NMR and MS. Their inhibitory

Discovery and synthesis of N2,N4-substitued- cycloalkyl[d]pyrimidine-2,4-diamine analogs: The first examples of small-molecular FGFR-1 activator

A series of novel, cycloalkyl-modified pazopanib analogs 2 and 3 were designed and synthesized. Their kinase modulatory effects on FGFR-1, VEGFR-2, PDGFR-β, and c-KIT were evaluated by the caliper mobility shift assay. Introduction of cycloalkyl into the pyrimidine linker of pazopanib almost abolished the four kinases inhibitory potency of compounds 2 and 3, but surprisingly, resulted in good activation effects on FGFR-1. Compounds 3d and 3g showed double-digit, nanomolar, selective activation effects on FGFR-1, and could be classified as first-generation small molecular activators of FGFR-1 kinase.

Reduction of nitroindazoles: Preparation of new amino and chloroamino derivatives

The synthesis of chloroaminoindazoles by the reduction of the nitro group of indazoles using stannous chloride in alcoholic acid solution is reported. Using catalytic hydrogenation with palladium the expected reduction to amino-indazoles occur.{A figure is presented}. Indazole Nitro Reduction Chlorination Aminochloroindazole Heterocycle.

SYNTHESIS OF SUBSTITUTED PYRAZOLO- AND PYRAZOLOPHENOTHIAZINE DERIVATIVES

The synthesis of new pyrazolo- and phenothiazines by the Bernthsen thionation of N-arylindazoles obtained using organometalic compounds is reported.

Synthesis of Pyrazoloacridin-9(10H)-ones

Eight pyrazoloacridin-9(10H)-ones were prepared in a three step procedure from 5- and 6-nitroindazoles.Palladium catalysed hydrogenation of nitroindazoles afforded the corresponding 5- and 6-aminoindazoles.These, in turn, reacted with o-chlorobenzoic acid under the conditions of the Ullman reaction to give anthranilic acids.Cyclisation of these acids by means of sulfuric acid led to the title compounds.If phosphoryl chloride was used, instead of sulfuric acid, a 9-chloroacridine derivative was obtained.All the compounds were characterised by 1H NMR spectroscopy.

SYNTHESIS OF 5-HYDROXY-4-NITROSOBENZOTRIAZOLES AND 6-HYDROXY-7-NITROSO-INDAZOLES AND THEIR SPLITTING INTO β-TRIAZOLYL- AND β-PYRAZOLYLACRYLIC ACIDS

5-Hydroxy-4-nitrosobenzotriazoles and 6-hydroxy-7-nitrosoindazoles were synthesized.By the action of benzenesulfonyl chloride in an alkaline medium, only 5-hydroxy-4-nitroso-2-phenyl-benzotriazole and 1-methyl-6-hydroxy-7-nitrosoindazole split into 5-carb