166402-16-0

Basic information

• Product Name: 6-Quinoxalinamine, 3-chloro-
• Synonyms: 6-Quinoxalinamine, 3-chloro-;3-Chloroquinoxalin-6-amine
• CAS NO: 166402-16-0
• Molecular Formula: C₈H₆ClN₃
• Molecular Weight: 179.61
• Mol File: 166402-16-0.mol

Chemical Properties

• Boiling Point: 339.6±37.0 °C(Predicted)
• Appearance: /
• Density: 1.445±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 0.66±0.10(Predicted)
• CAS DataBase Reference: 6-Quinoxalinamine, 3-chloro-(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Quinoxalinamine, 3-chloro-(166402-16-0)
• EPA Substance Registry System: 6-Quinoxalinamine, 3-chloro-(166402-16-0)

Safety Data

• Hazardous Substances Data: 166402-16-0(Hazardous Substances Data)

Upstream product

• 89898-96-4 2-Hydroxy-7-nitroquinoxaline 
• 1196-57-2 2-hydroxyquinoxaline 
• 1084-76-0 DNP-Gly 
• 251474-50-7 7-amino-3,4-dihydro-1H-quinoxalin-2-one 
• 98555-00-1 7-aminoquinoxalin-2(1H)-one 
• 89898-96-4 7-nitroquinoxaline-2(1H)-one 
• 55686-94-7 2-Chloro-7-nitroquinoxaline 

Relevant articles and documents

1, 4, 8-Triazaphenanthrene Derivatives For The Treatment Of Neurodegenerative Disorders

The invention relates to compounds of formula (I), particularly for the use thereof as a medicament, especially in the treatment or prevention of neurogenerative disorders. The invention also relates to the methods for producing said compounds, and to the

From simple quinoxalines to potent oxazolo[5,4-: F] quinoxaline inhibitors of glycogen-synthase kinase 3 (GSK3)

2,7-Disubstituted oxazolo[5,4-f]quinoxalines were synthesized from 6-amino-2-chloroquinoxaline in four steps (iodination at C5, substitution of the chloro group, amidation and copper-catalysed cyclization) affording 28 to 44% overall yields. 2,8-Disubstituted oxazolo[5,4-f]quinoxaline was similarly obtained from 6-amino-3-chloroquinoxaline (39% overall yield). For the synthesis of other oxazolo[5,4-f]quinoxalines, amidation was rather performed before substitution; moreover, time-consuming purification steps were avoided between the amines and the final products (38 to 54% overall yields). Finally, a more efficient method involving merging of the last two steps in a sequential process was developed to access more derivatives (37 to 65% overall yields). Most of the oxazolo[5,4-f]quinoxalines were evaluated for their activity on a panel of protein kinases, and a few 2,8-disubstituted derivatives proved to inhibit GSK3 kinase. While experiments showed an ATP-competitive inhibition on GSK3β, structure-activity relationships allowed us to identify 2-(3-pyridyl)-8-(thiomorpholino)oxazolo[5,4-f]quinoxaline as the most potent inhibitor with an IC50 value of about 5 nM on GSK3α.

New 6-Aminoquinoxaline Derivatives with Neuroprotective Effect on Dopaminergic Neurons in Cellular and Animal Parkinson Disease Models

Parkinson's disease (PD) is a neurodegenerative disorder of aging characterized by motor symptoms that result from the loss of midbrain dopamine neurons and the disruption of dopamine-mediated neurotransmission. There is currently no curative treatment for this disorder. To discover druggable neuroprotective compounds for dopamine neurons, we have designed and synthesized a second-generation of quinoxaline-derived molecules based on structure-activity relationship studies, which led previously to the discovery of our first neuroprotective brain penetrant hit compound MPAQ (5c). Neuroprotection assessment in PD cellular models of our newly synthesized quinoxaline-derived compounds has led to the selection of a better hit compound, PAQ (4c). Extensive in vitro characterization of 4c showed that its neuroprotective action is partially attributable to the activation of reticulum endoplasmic ryanodine receptor channels. Most interestingly, 4c was able to attenuate neurodegeneration in a mouse model of PD, making this compound an interesting drug candidate for the treatment of this disorder.