3176-63-4

Usage

Uses

Used in Pharmaceutical Industry:
4-Methyl (1H)indazole is used as a therapeutic agent for its anti-inflammatory, analgesic, and antipyretic properties, providing relief from inflammation, pain, and fever.
Used in Research and Development:
4-Methyl (1H)indazole is used as a research compound for studying its potential in treating various central nervous system disorders, such as neurodegenerative diseases and psychiatric disorders, due to its diverse pharmacological activities.
Used in Synthesis of New Pharmaceutical Compounds:
4-Methyl (1H)indazole is used as a building block in the synthesis of new pharmaceutical compounds with improved therapeutic properties, contributing to the ongoing research and development efforts in the pharmaceutical industry.

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

Upstream product

• 87-59-2 2,3-Dimethylaniline 
• 83-41-0 2,3-dimethylnitrobenzene 
• 95-52-3 2-Fluorotoluene 

Downstream Products

• 860007-80-3 4-methyl-1-(4-trifluoromethylphenyl)-1H-indazole 
• 1034874-85-5 2-amino-4-methylindazole 
• 33334-10-0 1-amino-3-phenylindazole 
• 1330064-82-8 C₁₄H₁₃N₃ 
• 1330064-48-6 C₂₂H₁₆ClF₃N₄O 
• 1438463-93-4 C₁₄H₁₁N₃O₂ 
• 1352415-05-4 methyl 4-methyl-1H-indazole-3-carboxylate 
• 885522-63-4 3-iodo-4-methyl-1H-indazole 

Relevant academic research and scientific papers

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.

NOVEL CATALYSTS

The present invention provides novel compounds and ligands that are useful in transition metal catalyzed cross-coupling reactions. For example, the compounds and ligands of the present invention are useful in palladium or gold catalyzed cross-coupling reactions.

BICYCLIC DERIVATIVES AS PPAR MODULATORS

The present invention is directed to compounds represented by the following structural formula, Formula (I), and stereoisomers, pharmaceutically acceptable salts, solvates and hydrates thereof, wherein: (a) R2 is selected from the group consisting of C0-C8 alkyl and C1-4- heteroalkyl; (b) X is selected from the group consisting of a single bond, O, S, S(O)2 and N; (c) U is an aliphatic linker wherein one carbon atom of the aliphatic linker is optionally replaced with O, NH or S, and wherein such aliphatic linker is optionally substituted with from one to four substituents each independently selected from R30; (d) Y is selected from the group consisting of C, O, S, NH and a single bond; and (e) E is C(R3)(R4)A or A.

Facile synthesis of 3-trimethylsilylindazoles by [3+2]cycloaddition reaction of lithium trimethylsilyldiazomethane with benzynes

[3+2]Cycloaddition reaction of lithium trimethylsilyldiazomethane with benzynes, generated from halobenzenes, gave the corresponding 3-trimethylsilylindazoles in good to moderate yields.

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.