6850-22-2

Basic information

• Product Name: 5-23-06-00185 (Beilstein Handbook Reference)
• Synonyms: 5-23-06-00185 (Beilstein Handbook Reference);6-Nitro-2-methyl-2H-indazole;NSC 131653;2-methyl-6-nitro-2H-indazole, 2-methyl-6-nitroindazole, 2-methyl-6-nitro-2H-indazole, 2-Methyl-6-nitro-2H-indazol, 2-methyl-6-nitro-indazole, 2-Methyl-6-nitro-indazol, 2-Methyl-6-nitroindazol
• CAS NO: 6850-22-2
• Molecular Formula: C₈H₇N₃O₂
• Molecular Weight: 177.16
• Mol File: 6850-22-2.mol
• Article Data: 15

Chemical Properties

• Melting Point: 158 °C
• Boiling Point: 364.5°Cat760mmHg
• Flash Point: 174.2°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 3.51E-05mmHg at 25°C
• Refractive Index: 1.676
• Storage Temp.: 2-8°C
• PKA: -1.81±0.30(Predicted)
• CAS DataBase Reference: 5-23-06-00185 (Beilstein Handbook Reference)(CAS DataBase Reference)
• NIST Chemistry Reference: 5-23-06-00185 (Beilstein Handbook Reference)(6850-22-2)
• EPA Substance Registry System: 5-23-06-00185 (Beilstein Handbook Reference)(6850-22-2)

Safety Data

• Hazardous Substances Data: 6850-22-2(Hazardous Substances Data)

Usage

Uses

Since the specific chemical composition and properties of 5-23-06-00185 are not provided in the summary, it is not possible to list its uses based on the given materials. However, the reference number can be used to look up the compound in the Beilstein Handbook to find information about its applications and potential uses in various industries.

InChI:InChI=1/C8H7N3O2/c1-10-5-6-2-3-7(11(12)13)4-8(6)9-10/h2-5H,1H3

Upstream product

• 77-78-1 dimethyl sulfate 
• 7597-18-4 6-nitroindazole 
• 74-88-4 methyl iodide 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 95-53-4 o-toluidine 
• 616-38-6 carbonic acid dimethyl ester 
• 2533-69-9 methyl 2,2,2-trichloroacetimidate 
• 99-55-8 2-methyl-5-nitroaniline 

Downstream Products

• 50593-30-1 2-methyl-2H-indazol-6-amine 
• 1311986-73-8 N²-(3-fluorophenyl)-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 
• 1311986-75-0 N²-(3-methoxyphenyl)-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 
• 1311986-79-4 N²-(3,5-dimethylphenyl)-N⁴-methyl-N⁴-(2-methyl-2H-indazol-6-yl)pyrimidine-2,4-diamine 
• 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 
• 132283-43-3 2-(2-Methyl-2H-indazol-6-ylamino)-benzoic acid 
• 52470-67-4 2-methyl-6-hydroxyindazole 
• 74209-41-9 3-bromo-2-methyl-6-nitro-2H-indazole 

Relevant articles and documents

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.

New nitroindazolylacetonitriles: Efficient synthetic access: Via vicarious nucleophilic substitution and tautomeric switching mediated by anions

New N-Alkyl-nitroindazolylacetonitriles were efficiently obtained via vicarious nucleophilic substitution of N-methyl-nitroindazoles with 4-chlorophenoxyacetonitrile. All compounds were fully characterized by NMR and mass spectroscopy techniques and the structures of some of them were additionally confirmed by X-ray diffraction analysis data. Tautomeric switching was observed in this series of nitroindazolylacetonitriles upon addition of basic anions followed by UV-Vis spectrophotometric and 1H-NMR titrations. The formation of tautomeric species induced by anionic species was endorsed by Density Functional Theory calculations.

One-pot synthesis of new 6-pyrrolyl-N-alkyl-indazoles from reductive coupling of N-alkyl-6-nitroindazoles and 2,5-hexadione

One-pot synthesis of 6-pyrrolyl-N-alkyl-indazoles by the reductive coupling of N-alkyl-6-nitroindazoles and 2,5-hexadione was investigated in the presence of different reducing agents (SnCl2/AcOH and In/AcOH in THF). Indazoles 5a-h and 6a-h wer

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.

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.

THIENO[3,2-D]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASES

Provided are a thieno[3,2-d]pyrimidine derivative of formula (I) or a pharmaceutically acceptable salt thereof having inhibitory activity for protein kinase, and a pharmaceutical composition comprising same for prevention and treatment of abnormal cell growth diseases.

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

Regioselective methylation of indazoles using methyl 2,2,2- trichloromethylacetimidate

An efficient and regio selective synthesis of substituted 2-methyl-2H-indazoles using a methyl 2,2,2-trichloroacetimidate is described.

An expedient, regioselective synthesis of novel 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]- and -[4,5-g]indazoles and their anticancer potential

Several novel 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]- and -[4,5-g]indazoles and their 6-alkyl and 8-alkyl derivatives have been synthesised in high overall yields starting from 5-nitro and 6-nitroindazoles in a three-step route involving the regioselective cyclisation of thioureidoindazoles and indazolyl dithiocarbamates as the key steps. Some assorted thiazoloindazoles have been screened for anticancer properties, which demonstrated the anticancer potential of at least one product, justifying its further follow-up.

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.