185316-58-9

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
5-PHENYL-1H-INDAZOLE is used as a building block for the synthesis of various pharmaceuticals and agrochemicals, due to its unique chemical structure and properties that can be further modified to create new compounds with specific therapeutic or pesticidal effects.
Used in Neurological and Psychiatric Disorders Treatment:
5-PHENYL-1H-INDAZOLE is used as a potential therapeutic agent for neurological and psychiatric disorders, given its potential to modulate specific biological pathways and receptors involved in these conditions.
Used in Coordination Chemistry:
5-PHENYL-1H-INDAZOLE is used as a ligand in coordination chemistry, where it can form complexes with metal ions, contributing to the development of new materials with unique properties and potential applications in various fields.
Used in Electronics and Material Science:
5-PHENYL-1H-INDAZOLE is used in the development of electronic materials and devices, owing to its electronic properties that can be harnessed to improve the performance of semiconductors, sensors, and other electronic components.

InChI:InChI=1/C13H10N2/c1-2-4-10(5-3-1)11-6-7-13-12(8-11)9-14-15-13/h1-9H,(H,14,15)

Upstream product

• 210556-89-1 2-formyl-4-phenyl-cyclohexanone 
• 864771-44-8 1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate 
• 108-86-1 bromobenzene 

Downstream Products

• 1338792-00-9 3-(5-phenyl-1H-indazol-3-yl)benzenesulfonamide 
• 1338795-62-2 3-iodo-5-phenyl-1H-indazole 

Relevant academic research and scientific papers

5-phenylindazole

The title compound, C13H10N2, packs in chains along the a axis via N - H...N hydrogen bonds that are stronger and more linear than those observed in unsubstituted indazole. These chains are linked by C - H...N and C - H...phenyl contacts along b, giving rise to a wave-like structure.

Visible-Light-Mediated N-Desulfonylation of N-Heterocycles Using a Heteroleptic Copper(I) Complex as a Photocatalyst

A photoredox protocol that uses a heteroleptic Cu (I) complex, [Cu(dq)(BINAP)]BF4, has been developed for the photodeprotection of benzenesulfonyl-protected N-heterocycles. A range of substrates was examined, including indazoles, indoles, pyrazoles, and benzimidazole, featuring both electron-rich and electron-deficient substituents, giving good yields of the N-heterocycle products with broad functional group tolerance. This transformation was also found to be amenable to flow reaction conditions.

Discovery of inhibitors of the mitotic kinase TTK based on N-(3-(3-sulfamoylphenyl)-1H-indazol-5-yl)-acetamides and carboxamides

TTK kinase was identified by in-house siRNA screen and pursued as a tractable, novel target for cancer treatment. A screening campaign and systematic optimization, supported by computer modeling led to an indazole core with key sulfamoylphenyl and acetamido moieties at positions 3 and 5, respectively, establishing a novel chemical class culminating in identification of 72 (CFI-400936). This potent inhibitor of TTK (IC50 = 3.6 nM) demonstrated good activity in cell based assay and selectivity against a panel of human kinases. A co-complex TTK X-ray crystal structure and results of a xenograft study with TTK inhibitors from this class are described.

KINASE INHIBITORS AND METHOD OF TREATING CANCER WITH SAME

The present teachings provide a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof. Also described are a pharmaceutical composition and method of use thereof.