28519-78-0

Usage

Chemical class

Indazole

Usage

Synthesis of pharmaceuticals and organic compounds

Biological and pharmacological activities

Potential applications in drug discovery and development

Phenylmethyl group

May contribute to interactions with biological targets, valuable building block in medicinal chemistry and drug design.

Upstream product

• 874-05-5 3-aminoindazole 
• 100-44-7 benzyl chloride 
• 1219024-53-9 2-(2-(diphenylmethylene)hydrazinyl)benzonitrile 
• 132475-60-6 2-bromobenzamidoxime 
• 408322-07-6 3-amino-1-benzylideneaminoindazole 
• 408322-05-4 1,3-diaminoindazole 
• 185011-20-5 1-benzylideneamino-3-nitroindazole 

Relevant academic research and scientific papers

Cascade Synthesis of Kinase-Privileged 3-Aminoindazoles via Intramolecular N-N Bond Formation

3-Aminoindazoles are privileged scaffolds for bioactive drug-like molecules. In this study, a microwave-assisted cascade reaction for the synthesis of N-1 substituted 3-aminoindazoles with yields up to 81% has been developed. Starting from 3-(2-bromoaryl)-1,2,4-oxadiazol-5(4H)-ones, the reaction exhibits a broad substrate scope including anilines, aliphatic amines, and sulfonamides and bypasses selectivity issues between N-1 and 3-amino group. Furthermore, the Differential Scanning Fluorimetry screen of a kinase panel demonstrated the value of targeting N-1 substituted 3-aminoindazoles as kinase-biased fragments.

INHIBITORS OF CYCLIN-DEPENDENT KINASE 7 (CDK7)

The present invention provides novel compounds of Formula (I) and pharmaceutically acceptable salts, solvates, hydrates, tautomers, stereoisomers, isotopically labeled derivatives, and compositions thereof. Also provided are methods and kits involving the compounds or compositions for treating or preventing proliferative diseases (e.g., cancers (e.g., leukemia, melanoma, multiple myeloma), benign neoplasms, angiogenesis, inflammatory diseases, autoinflammatory diseases, and autoimmune diseases) in a subject. Treatment of a subject with a proliferative disease using a compound or composition of the invention may inhibit the aberrant activity of cyclin-dependent kinase (e.g., CDK7), and therefore induce cellular apoptosis and/or inhibit transcription in the subject.

Assembly of Primary (Hetero)Arylamines via CuI/Oxalic Diamide-Catalyzed Coupling of Aryl Chlorides and Ammonia

A general and practical catalytic system for aryl amination of aryl chlorides with aqueous or gaseous ammonia has been developed, with CuI as the catalyst and bisaryl oxalic diamides as the ligands. The reaction proceeds at 105-120°C to provide a diverse set of primary (hetero)aryl amines in high yields with various functional groups.

Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts

A method for the Pd-catalyzed arylation of ammonia with a wide range of aryl and heteroaryl halides, including challenging five-membered heterocyclic substrates, is described. Excellent selectivity for monoarylation of ammonia to primary arylamines was achieved under mild conditions or at rt by the use of bulky biarylphosphine ligands (L6, L7, and L4) as well as their corresponding aminobiphenyl palladacycle precatalysts (3a, 3b, and 3c). As this process requires neither the use of a glovebox nor high pressures of ammonia, it should be widely applicable.

Two-step synthesis of substituted 3-aminoindazoles from 2-bromobenzonitriles

A general two-step synthesis of substituted 3-aminoindazoles from 2-bromobenzonitriles involving a palladium-catalyzed arylation of benzophenone hydrazone followed by an acidic deprotection/cyclization sequence is described. This procedure offers a general and efficient alternative to the typical S NAr reaction of hydrazine with o-fluorobenzonitriles.

INDAZOLE DERIVATIVES

The invention is concerned with novel indazole derivatives of formula (I) wherein R1, R2, R3, R4, R5, R6, X and Y are as defined in the description and in the claims, as well as physiologic

Synthesis and oxidation of 1,3-diamino- and 1-amino-3-azidoindazoles

The animation of 3-amino- and 3-azidoindazoles by hydroxylamine-O-sulfonic acid in an alkaline medium yields previously unreported 1,3-diamino- and 1-amino-3-azidoindazoles. These products undergo slow autoxidation in chloroform solution to give 4-aminobe