Quinoxalinedione

Quinoxalinedione is an organic compound with the formula C₆H₄(NH)₂(CO)₂. It is a colorless solid that is soluble in polar organic solvents. Quinoxalinediones are a family of related compounds sharing the same bicyclic core. Various quinoxalinediones are drugs.^[1]

Quinoxalinedione

Names
Preferred IUPAC name 1,4-Dihydroquinoxaline-2,3-dione
Identifiers
CAS Number	15804-19-0 Y
3D model (JSmol)	Interactive image
ChemSpider	9644059
ECHA InfoCard	100.036.259
EC Number	239-901-0
PubChem CID	11469229
UNII	APO55IZ9E1 Y
CompTox Dashboard (EPA)	DTXSID9065946
InChI InChI=1S/C8H4N2O2/c11-7-8(12)10-6-4-2-1-3-5(6)9-7/h1-4H Key: SEPKUNXLGWMPHL-UHFFFAOYSA-N
SMILES C1=CC2=NC(=O)C(=O)N=C2C=C1
Properties
Chemical formula	C8H6N2O2
Molar mass	162.15
Appearance	white solid
Density	1.549 g/cm3
Melting point	> 300 °C (572 °F; 573 K)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H318, H319, H335
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Synthesis and structure

Quinoxalinedione is produced by condensation of dimethyloxalate and o-phenylenediamine:

C₂O₂(OMe)₂ + C₆H₄(NH₂)₂ → C₆H₄(NH)₂(CO)₂ + 2 MeOH

The compound exists in solution and the solid state predominantly as the diamide form.^[2] Some reactions of the compound indicate a role for the diol tautomer.

Drugs based on quinoxalinediones

Quinoxalinediones act as antagonists of the AMPA, kainate, and/or NMDA receptors of the ionotropic glutamate receptor family.^[3][4][5][6] Examples include the following:

• ACEA-1011
• Becampanel
• CNQX
• DNQX
• Fanapanel (MPQX)
• Licostinel (ACEA-1021)
• NBQX
• PNQX
• YM90K
• Zonampanel

A drug closely related to the quinoxalinediones, but possessing a quinazoline-2,4-dione structure instead, is selurampanel. Caroverine is another closely related drug to the above, but instead containing a quinoxaline-2-one structure.