57614-16-1

Basic information

• Product Name: 5-Methyl-3-Phenyl-1H-Indazole
• Synonyms: 5-Methyl-3-Phenyl-1H-Indazole;1H-Indazole, 5-methyl-3-phenyl-;5-Methyl-3-Phenyl-1H-Indazole(WXC05304)
• CAS NO: 57614-16-1
• Molecular Formula: C₁₄H₁₂N₂
• Molecular Weight: 208.25848
• Mol File: 57614-16-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 133 °C
• Boiling Point: 417.0±14.0 °C(Predicted)
• Appearance: /
• Density: 1.178±0.06 g/cm3(Predicted)
• PKA: 13.89±0.40(Predicted)
• CAS DataBase Reference: 5-Methyl-3-Phenyl-1H-Indazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methyl-3-Phenyl-1H-Indazole(57614-16-1)
• EPA Substance Registry System: 5-Methyl-3-Phenyl-1H-Indazole(57614-16-1)

Safety Data

• Hazardous Substances Data: 57614-16-1(Hazardous Substances Data)

Upstream product

• 17852-28-7 2-amino-5-methylbenzophenone 
• 885518-92-3 3-iodo-5-methyl-1H-indazole 
• 1259851-81-4 tert-butyl 3-iodo-5-methyl-1H-indazole-1-carboxylate 
• 98-80-6 phenylboronic acid 

Relevant articles and documents

ML212: A small-molecule probe for investigating fluconazole resistance mechanisms in Candida albicans

The National Institutes of Health Molecular Libraries and Probe Production Centers Network (NIH-MLPCN) screened >300,000 compounds to evaluate their ability to restore fluconazole susceptibility in resistant Candida albicans isolates. Additional counter screens were incorporated to remove substances inherently toxic to either mammalian or fungal cells. A substituted indazole possessing the desired bioactivity profile was selected for further development, and initial investigation of structure-activity relationships led to the discovery of ML212.

Methods for treating an inflammatory condition or inhibiting JNK

This invention is generally directed to Indazole Derivatives having the following structure: 1 or pharmaceutically acceptable salt thereof, wherein R1, R2 and A are as defined herein. Such compounds have utility in the treatment of a wide range of diseases and disorders that are responsive to JNK inhibition, such as an inflammatory disease or disorder. Thus, methods of treating such diseases and disorders are also disclosed, as are pharmaceutical compositions containing one or more compounds of the above compounds.

Synthesis of 3-aryl-1-[(4-phenyl-1-piperazinyl)butyl]indazole derivatives and their affinity to 5-HT(1A) serotonin and dopamine D1 receptors

Eight 3-arylindazole derivatives have been synthesized and their affinity to 5-HT(1A) serotonin and D1 dopamine receptors was investigated by radioligand analysis. Quantitative structure-activity relationships were studied using the Free-Wilson model. An increase in affinity to dopamine D1 receptors within substituents Br > Cl > CH3 at the 5-position of the 3- arylindazole molecule has been observed. Addition of a chlorine atom to the ortho-position the of phenyl ring let to even highes activity. Replacement of the hydrogen atom at the first position of the 3-arylindazole on the (phenylpiperazine)butyl substituent caused an increase of affinity and did not change the trends of affinity dependence on structure. An inverse dependence on the structure of the studied compounds was observed for the serotonin 5-HT(1A) receptors. Compounds containing a methyl group at the 5- position of molecule were more active than compounds containing halogens. A chlorine atom at the ortho-position of the phenyl ring decreased affinity. Replacement of the hydrogen atom at the first position of the molecule on the phenylpiperazine)butyl substituent led to an increase in affinity. Selectivity of the studied compounds varied within a wide range. Generally, the presence of the 3-aryl-indazole fragment in the new buspirone analogues increased their affinity to dopamine receptors and reduced their affinity to serotonin receptors. Compounds containing a bromine atom in the 3- arylindazole moiety may be promising ligands for D1 receptors.