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.
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.Saied M. Soliman, Jörg Albering, Morsy A.M. Abu-Youssef "Low temperature X-ray molecular structure, tautomerism and spectral properties of 2,3-dihydroxyquinoxaline" Journal of Molecular Structure 2013, vol. 1053, pp. 48–60. 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. 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.
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