221681-89-6

Basic information

• Product Name: 1H-Indazol-7-aMine,5-chloro-
• Synonyms: 1H-Indazol-7-aMine,5-chloro-;7-AMino-5-chloro-1H-indazole;5-Chloro-1H-indazol-7-aMine;7-amino-5-chloroindazole;5-Chloro-1H-indazole-7-amino
• CAS NO: 221681-89-6
• Molecular Formula: C7H6ClN3
• Molecular Weight: 167.59564
• Mol File: 221681-89-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Indazol-7-aMine,5-chloro-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indazol-7-aMine,5-chloro-(221681-89-6)
• EPA Substance Registry System: 1H-Indazol-7-aMine,5-chloro-(221681-89-6)

Safety Data

• Hazardous Substances Data: 221681-89-6(Hazardous Substances Data)

Usage

Structure

A derivative of indazole with a chlorine atom in the fifth position of the indazole ring

Type

A chemical compound

Applications

Potential use in pharmaceutical and chemical research as an intermediate in the synthesis of various organic compounds, and in the development of new drugs or other bioactive molecules.

Safety

Proper handling and safety precautions should be taken when working with 1H-Indazol-7-aMine,5-chloro-.

Upstream product

• 41926-18-5 5-chloro-7-nitro-1⁽²⁾H-indazole 
• 570-24-1 2-Methyl-6-nitroaniline 
• 62790-50-5 4-chloro-2-methyl-6-nitrophenylamine 

Relevant articles and documents

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.