6850-23-3

Usage

Uses

Used in Pharmaceutical Industry:
1-METHYL-6-NITRO-1H-INDAZOLE is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and improving existing ones.
Used in Organic Compounds Synthesis:
It serves as a key component in the synthesis of organic compounds, facilitating the creation of a wide range of chemical products.
Used in Dye Industry:
1-METHYL-6-NITRO-1H-INDAZOLE is used in the development of dyes, playing a crucial role in the production of colorants for various applications.
Used in Agrochemicals Manufacturing:
1-METHYL-6-NITRO-1H-INDAZOLE is utilized in the manufacturing process of agrochemicals, aiding in the production of substances that protect and enhance crop yields.
Used in Chemical Reactions:
Due to its high reactivity, 1-METHYL-6-NITRO-1H-INDAZOLE is employed in various chemical reactions, enabling the formation of new compounds and contributing to advancements in the chemical sciences.

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

Upstream product

• 77-78-1 dimethyl sulfate 
• 7597-18-4 6-nitroindazole 
• 74-88-4 methyl iodide 
• 124-41-4 sodium methylate 
• 5401-94-5 5-nitroindazole 
• 52142-72-0 1,2-dimethyl-6-nitro-indazolium; iodide 

Downstream Products

• 74728-65-7 1-methyl-1H-indazol-6-ylamine 
• 74209-32-8 3-bromo-1-methyl-6-nitro-1H-indazole 
• 159597-47-4 1-methyl-6-p-methoxyphenylamino-1H-indazole 
• 118933-92-9 6-hydroxy-1-methyl-1H-indazole 
• 1620816-62-7 1-methyl-6-nitro-3-phenyl-1H-indazole 
• 1620816-65-0 1-methyl-6-nitro-3,7-diphenyl-1H-indazole 
• 1620816-75-2 1-methyl-4-nitro-3-phenyl-7-p-tolyl-1H-indazole 
• 724766-98-7 1-methyl-1H-indazole-5,6-diyldiamine 
• 132283-42-2 2-(1-Methyl-1H-indazol-6-ylamino)-benzoic acid 

Relevant academic research and scientific papers

AMI, an Indazole Derivative, Improves Parkinson’s Disease by Inhibiting Tau Phosphorylation

Dopaminergic neuronal loss is the main pathological character of Parkinson’s disease (PD). Abnormal tau hyperphosphorylation will lead to dopaminergic neuronal loss. An indazole derivative 6-amino-1-methyl-indazole (AMI) successfully synthesized to inhibit tau hyperphosphorylation may exert a neuroprotective effect. The in vitro study showed that AMI effectively increased cell viability and alleviated the apoptosis induced by MPP+ in SH-SY5Y cells. In addition, AMI treatment significantly decreased the expression of p-tau and upstream kinases GSK-3β. In the MPTP-induced PD mice models, we found AMI apparently preserved dopaminergic neurons in the substantia nigra and improved the PD behavioral symptoms. Our results demonstrate that AMI exerts a neuroprotective effect by inhibiting tau hyperphosphorylation, representing a promising new candidate for PD treatment.

ARYL-PHOSPHORUS-OXYGEN COMPOUND AS EGFR KINASE INHIBITOR

Disclosed is a class of new aryl-phosphorus-oxygen compounds as shown in formula (I) as EGFR kinase inhibitors, and pharmaceutically acceptable salts thereof.

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.

Palladium-Catalyzed Oxidative Arylation of 1H-Indazoles with Arenes

A simple method for the direct Pd(OAc)2-catalyzed oxidative arylation of inactivated 1H-indazole derivatives with simple arenes is reported. This method exhibits good reaction efficiency and good functional-group tolerance. Using the developed method, 28 arylated products were prepared in yields up to 80 %.

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.

THERAPEUTIC INDAZOLES

The invention provides compounds of formula (I): and salts thereof wherein R1-R5 have any of the meanings described in the specification. The compounds are useful for treating bacterial infections (e.g. tuberculosis).

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.

Synthesis and Some Transformations of 7-(Fur-2-yl)-1-methyl-1H-pyrazolo[4,3-g][1,3]benzothiazole

N-Methylation of 5-nitro-1H-indazole in a KOH–DMSO system resulted in a mixture of 1-methyl-5(6)-nitroindazoles in a ratio of 1: 2. Reduction of the isomers with tin in concentrated hydrochloric acid afforded pure 1-methyl-1H-indazole-6-amine. Condensation of the latter with furoyl chloride in 2-propanol yielded N-(1-methylindazol-6-yl)furan-2-carboxamide, treatment of which with an excess of P2S5 in anhydrous pyridine gave the corresponding carbothioamide. 7-(Fur-2-yl)-1-methyl-1H-pyrazolo[4,3-g][1,3]benzothiazole was synthesized by Jacobson oxidation of N-(1-methylindazol-6-yl) furan-2-carbothioamide with potassium ferricyanide in an alkaline medium. Some transformations of 7-(fur-2-yl)-1-methyl-1H-pyrazolo[4,3-g][1,3]- benzothiazole such as formylation and acylation were performed.

Wnt signal pathway inhibitor and use thereof

The invention relates to heterocyclic compounds with Wnt signal channel inhibition activity, particularly including compounds, pharmaceutically acceptable salts, various isotopes, various isomers or various crystal structures thereof having a structure represented by a general formula I (shown in the specification). By the compounds and a composition of the compounds, a Wnt signal channel can be effectively inhibited and diseases related to the Wnt signal channel can be treated or prevented.

Indazole derivative as well as preparation method and application thereof

The invention relates to an indazole derivative. The molecular structure of the derivative is as shown in the following formula (I). The compound disclosed by the invention has outstanding effects of inhibiting the activity of tau proteins, reducing the phosphorylation level of the tau proteins, resisting neuronal apoptosis and preventing and treating neurodegenerative diseases.