74728-65-7

Basic information

• Product Name: 1-METHYL-1H-INDAZOL-6-YLAMINE
• Synonyms: 6-AMINO-1-METHYLINDAZOLE;1-METHYL-1H-INDAZOL-6-YLAMINE;1-Methyl-1H-indazol-6-amine;6-Amino-1-methyl-1H-indazole;1-methyl-1H-indazole-6-amine;6-AMino-1-Methyl-1H-indaz...;1-Methyl-1H-indazole-6-ylamine
• CAS NO: 74728-65-7
• Molecular Formula: C₈H₉N₃
• Molecular Weight: 147.18
• Product Categories: pharmacetical;Building Blocks;Indazole
• Mol File: 74728-65-7.mol
• Article Data: 24

Chemical Properties

• Melting Point: 172-173
• Boiling Point: 321.6°C at 760 mmHg
• Flash Point: 148.3°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 0.000295mmHg at 25°C
• Refractive Index: 1.667
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 1-METHYL-1H-INDAZOL-6-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-1H-INDAZOL-6-YLAMINE(74728-65-7)
• EPA Substance Registry System: 1-METHYL-1H-INDAZOL-6-YLAMINE(74728-65-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 74728-65-7(Hazardous Substances Data)

Usage

General Description

1-Methyl-1H-indazol-6-ylamine, also known as 1-methyl-3H-indazole-3-amine, is a chemical compound with the molecular formula C8H8N2. It is an aromatic amine with a substituted indazole ring structure. This chemical is a potential intermediate for the synthesis of pharmaceutical compounds and organic materials. It is used in the research and development of various drugs and can also be used as a building block for the preparation of other chemical compounds. Its unique structure and properties make it a valuable and versatile compound for use in organic synthesis and drug discovery.

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

Upstream product

• 6850-23-3 1-methyl-6-nitro-1H-indazole 
• 64-17-5 ethanol 
• 77-78-1 dimethyl sulfate 
• 7597-18-4 6-nitroindazole 
• 74-88-4 methyl iodide 

Downstream Products

• 132283-42-2 2-(1-Methyl-1H-indazol-6-ylamino)-benzoic acid 
• 118933-92-9 6-hydroxy-1-methyl-1H-indazole 
• 159597-47-4 1-methyl-6-p-methoxyphenylamino-1H-indazole 
• 128056-49-5 2-(4-chlorophenyl)-5,10-dihydro-10-methyl-2H-dipyrazolo<4,3-c:3',4'-f>quinolin-3-one 
• 1122710-35-3 2-chloro-N-(1-methyl-1H-indazol-6-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine 

Relevant articles and documents

Discovery of 1-(1H-indazol-4-yl)-3-((1-phenyl-1H-pyrazol-5-yl)methyl) ureas as potent and thermoneutral TRPV1 antagonists

A series of 1-indazol-3-(1-phenylpyrazol-5-yl)methyl ureas were investigated as hTRPV1 antagonists. The structure–activity relationship study was conducted systematically for both the indazole A-region and the 3-trifluoromethyl/t-butyl pyrazole C-region to optimize the antagonism toward the activation by capsaicin. Among them, the antagonists 26, 50 and 51 displayed highly potent antagonism with Ki(CAP) = 0.4–0.5 nM. Further, in vivo studies in mice indicated that these derivatives both antagonized capsaicin induced hypothermia, consistent with their in vitro activity, and themselves did not induce hyperthermia. In the formalin model, 51 showed anti-nociceptive activity in a dose-dependent manner.

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.

PRMT5 INHIBITORS AND USES THEREOF

Described herein are compounds of Formula (I), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.