698-24-8

Usage

Uses

Used in Pharmaceutical Industry:
6-METHYL (1H)INDAZOLE is used as a building block for the synthesis of various pharmaceuticals due to its potential biological activities, including its antifungal, antiviral, and anticancer properties. Its incorporation in drug development can lead to the creation of novel therapeutic agents targeting a range of diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 6-METHYL (1H)INDAZOLE is used as a key component in the development of compounds with pesticidal properties, leveraging its biological activity to protect crops from fungal and viral infections, thereby enhancing agricultural productivity.
Used in Chemical Research:
6-METHYL (1H)INDAZOLE serves as a reagent in chemical research, facilitating the exploration of new chemical reactions and the synthesis of complex organic molecules. Its presence in laboratories aids scientists in advancing the understanding of chemical properties and reactions.
Used in Production of Fine Chemicals:
6-METHYL (1H)INDAZOLE is utilized in the production of fine chemicals, where its unique properties contribute to the creation of high-quality specialty chemicals used in various industries, such as fragrances, dyes, and coatings.
Available in various purity grades, 6-METHYL (1H)INDAZOLE can be adapted to a wide range of applications, making it a valuable asset in the fields of chemistry and biology.

InChI:InChI=1/C8H8N2/c1-6-2-3-7-5-9-10-8(7)4-6/h2-5H,1H3,(H,9,10)

Upstream product

• 71114-52-8 N-(2,5-dimethylphenyl)benzamide 
• 343791-82-2 1-acetyl-6-methyl-1H-indazole 
• 95-78-3 2,5-Dimethylaniline 
• 698-27-1 4-methylsalicylaldehyde 
• 824-54-4 2-bromo-4-methylbenzaldehyde 

Downstream Products

• 885518-96-7 3-iodo-6-methyl-1H-indazole 
• 858227-11-9 methyl 6-methyl-1H-indazole-3-carboxylate 
• 1126424-54-1 2-methyl-2-propanyl 6-(bromomethyl)-1H-indazole-1-carboxylate 
• 40500-17-2 6-methyl-1-(2-nitro-phenyl)-1H-indazole 
• 1257535-50-4 3-iodo-1,6-dimethyl-1H-indazole 

Relevant academic research and scientific papers

A novel copper-catalyzed, hydrazine-free synthesis of N-1 unsubstituted 1H-indazoles using stable guanylhydrazone salts as substrates

A CuI-catalyzed, hydrazine-free transformation of 2-(2-bromoarylidene)guanylhydrazone hydrochlorides using Cs2CO3 as a base and DMEDA as a ligand at 120 °C for 5 h delivers substituted 1H-indazoles with yields up to 75%. The C,N double bond configuration of the substrates was determined by NMR experiments and quantum chemical calculations. The reaction mechanism was studied using quantum chemical calculations.

Synthesis, antifungal activity and qsar of novel pyrazole amides as succinate dehydrogenase inhibitors

We design and synthesize a series of novel pyrazole amides based on the commercialized fungicides and our previous work. The antifungal activity was tested in vitro by mycelial growth inhibition assay. The results show that all the compounds are of antifungal activities against the tested fungi at different levels. Among them, N-(2-(7-bromo-5-chloro-1H-indazol-1-yl)phenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (Vk) exhibited higher antifungal activity than boscalid against two fungi. Molecular docking study revealed that the carbonyl oxygen atom of Vk forms two hydrogen bonds toward the hydroxyl hydrogens of TYR58 and TRP173.

Inhibition of the Cysteine Protease Human Cathepsin L by Triazine Nitriles: Amide???Heteroarene π-Stacking Interactions and Chalcogen Bonding in the S3 Pocket

We report an extensive “heteroarene scan” of triazine nitrile ligands of the cysteine protease human cathepsin L (hCatL) to investigate π-stacking on the peptide amide bond Gly67–Gly68 at the entrance of the S3 pocket. This heteroarene???peptide bond stacking was supported by a co-crystal structure of an imidazopyridine ligand with hCatL. Inhibitory constants (Ki) are strongly influenced by the diverse nature of the heterocycles and specific interactions with the local environment of the S3 pocket. Binding affinities vary by three orders of magnitude. All heteroaromatic ligands feature enhanced binding by comparison with hydrocarbon analogues. Predicted energetic contributions from the orientation of the local dipole moments of heteroarene and peptide bond could not be confirmed. Binding of benzothienyl (Ki=4 nm) and benzothiazolyl (Ki=17 nm) ligands was enhanced by intermolecular C?S???O=C interactions (chalcogen bonding) with the backbone C=O of Asn66 in the S3 pocket. The ligands were also tested for the related enzyme rhodesain.

A general synthesis of diversely substituted indazoles and hetero-aromatic derivatives from o-halo-(het)arylaldehydes or -phenones

A set of variously substituted indazoles and hetero-aromatic derivatives were synthesized from o-halo-(het)arylaldehydes using a palladium catalyzed amination followed by cyclization. Starting from phenones, this process was extended to give 3-substituted indazoles. Moreover, N-1-substituted-indazoles can be reached by this strategy using an optional selective N-1-alkylation step during the process. This methodology offers a general and easy route for the synthesis of regioselectively substituted indazoles.

a-AMINO ACID DERIVATIVE AND PHARMACEUTICAL COMPRISING THE SAME AS ACTIVE INGREDIENT

The present invention provides novel α-amino acid derivatives of formula (1): (wherein, R1, R2, R3, R4, X and Y are as defined in the claims) or pharmaceutically acceptable salts, prodrugs or solvates thereof. T

Inhibition of neuronal nitric oxide synthase by 7-methoxyindazole and related substituted indazoles

The synthesis and pharmacological evaluation of methoxyindazoles as new inhibitors of neuronal nitric oxide synthase are presented. The 7-methoxyindazole, although less potent than 7-NI, is the most active compound of the series in an in vitro enzymatic assay of neuronal nitric oxide synthase activity. This result shows that the nitro-substitution is not indispensable to the biological activity of the indazole ring. 7-Methoxyindazole possesses in vivo NOS inhibitory as well and related antinociceptive properties.

A Novel Approach to 1H-Indazoles via Arylazosulfides

Treatment of variously substituted (o-alkylaryl)azosulfides 1a-n with potassium tert-butoxide in DMSO at room temperature smoothly furnishes 1H-indazoles 2a-n.

Phase Transfer Catalyzed Synthesis of Indazoles from o-Alkylbenzenediazonium Tetrafluoroborates

Reaction of o-methyl- and o-ethylbenzenediazonium tetrafluoroborates with two equivalents of potassium acetate and five mole percent of 18-crown-6 in ethanol-free chloroform produce indazoles in good to excellent yields.Indazoles bearing either electron-withdrawing or electron-donating substituents may be prepared.

Aromatic Diazonium Salts, X. - A One-Pot Procedure for the Jacobson Synthesis of Indazole

Procedures are described for a one-pot synthesis of 1H-indazole and substituted indazoles 3 in good yield (Table 1) from o-toluidines 2, alkyl nitrite or nitrous oxides, potassium acetate, and acetic anhydride in benzene.The spectroscopic properties of substituted indazoles (Tables 2-4) are discussed. - 4-Phenylcinnoline (18) is prepared by the same procedure from o-(α-methylenebenzyl)aniline.