127710-79-6

Basic information

• Product Name: 8-Chloro-1-phenyl-4-piperazin-1-yl-[1,2,4]triazolo[4,3-a]quinoxaline
• Synonyms: 8-Chloro-1-phenyl-4-piperazin-1-yl-[1,2,4]triazolo[4,3-a]quinoxaline
• CAS NO: 127710-79-6
• Molecular Weight: 364.837
• Mol File: 127710-79-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 8-Chloro-1-phenyl-4-piperazin-1-yl-[1,2,4]triazolo[4,3-a]quinoxaline(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Chloro-1-phenyl-4-piperazin-1-yl-[1,2,4]triazolo[4,3-a]quinoxaline(127710-79-6)
• EPA Substance Registry System: 8-Chloro-1-phenyl-4-piperazin-1-yl-[1,2,4]triazolo[4,3-a]quinoxaline(127710-79-6)

Safety Data

• Hazardous Substances Data: 127710-79-6(Hazardous Substances Data)

Upstream product

• 2958-87-4 2,3,6-trichloro-quinoxaline 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 91895-34-0 2,6-dichloro-3-hydrazinoquinoxaline 
• 6639-79-8 6-chloroquinoxaline-2,3(1H,4H)-dione 
• 110-85-0 piperazine 
• 91895-38-4 4,8-dichloro-1-phenyl<1,2,4>triazolo<4,3-a>quinoxaline 

Relevant articles and documents

4-Aminotriazoloquinoxalines. A Novel Class of Potent Adenosine Receptor Antagonists and Potential Rapid-Onset Antidepressants

A series of 4-aminotriazoloquinoxalines has been prepared.Many compounds from this class reduce immobility in Porsolt's behavioral despair model in rats upon acute administration and may therefore have therapeutic potential as novel and rapid acting antidepressant agents.Optimal activity in this test is associated with hydrogen, CF3, or small alkyl groups in the 1-position, with NH2, NH-acetyl, or amines substituted with small alkyl groups in the 4-position, and with hydrogen or 8-halogen substituents in the aromatic ring.Furthermore, many of these 4-aminoquinoxalines bind avidly, and in some cases very selectively, to adenosine A1 and A2 receptors.A1 affinity of these compounds was measured by their inhibition of tritiated CHA (N6-cyclohexyladenosine) binding in rat cerebral cortex membranes and A2 affinity by their inhibition of tritiated NECA (5'-(N-ethylcarbamoyl)adenosine) binding to rat striatal homogenate in the presence of cold N6-cyclopentyladenosine.Structure-activity relationship (SAR) studies show that best A1 affinity is associated with ethyl, CF3, or C2F5 in the 1-position, NH-iPr or NH-cycloalkyl in the 4-position, and with an 8-chloro substituent.Affinity at the A2 receptor is mostly dependent on the presence of an NH2 group in the 4-position and is enhanced by phenyl, CF3, or ethyl in the 1-position.The most selective A1 ligand by a factor of >3000 is 121 (CP-68,247; 8-chloro-4-(cyclohexylamino)-1-(trifluoromethyl)triazoloquinoxaline) with an IC50 of 28 nM at the A1 receptor.The most potent A2 ligand is 128 (CP-66,713; 4-amino-8-chloro-1-phenyltriazoloquinoxaline) with an IC50 of 21 nM at the A2 receptor and a 13-fold selectivity for this receptor.Representatives from this series appear to act as antagonists at both A1 and A2 receptors since they antagonize the inhibiting action of CHA on norepinephrine-stimulated cAMP formation in fat cells and they decrease cAMP accumulation induced by adenosine in limbic forebrain slices.Thus certain members of this 4-aminotriazoloquinoxaline series are among the most potent and A1 or A2 selective non-xanthine adenosine antagonists known.