ⓘ Quinoxalinedione is an organic compound with the formula C 6 H 4 2 2. It is a colorless solid that is soluble in polar organic solvents. Quinoxalinediones are a ..

                                     

ⓘ Quinoxalinedione

Quinoxalinedione is an organic compound with the formula C 6 H 4 2 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. Synthesis and structure

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

C 2 O 2 OMe 2 + C 6 H 4 NH 2 → C 6 H 4 NH 2 CO 2 + 2 MeOH

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

                                     

2. 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:

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

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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