Quinoxalinedione

Quinoxalinedione
Identifiers
15804-19-0
Properties
C8H6N2O2
Molar mass 162.15
Appearance white solid
Density 1.549 g/cm3
Melting point > 300 C
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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 condensatoin 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.[1] 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.[2][3][4] Examples include the following:

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.

References

  1. ↑ 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. doi:10.1016/j.molstruc.2013.09.005
  2. ↑ Ashley, M.J. (2010). Traumatic Brain Injury: Rehabilitation, Treatment, and Case Management, Third Edition. CRC Press. p. 142. ISBN 978-1-4398-4982-8. Retrieved 2015-01-01.
  3. ↑ Turski, L.; Schoepp, D.D.; Cavalheiro, E.A. (2001). Excitatory Amino Acids: Ten Years Later. Biomedical and health research (in Italian). IOS Press. p. 38. ISBN 978-1-58603-072-8. Retrieved 2015-01-01.
  4. ↑ Offermanns, S.; Rosenthal, W. (2008). Encyclopedia of Molecular Pharmacology. Encyclopedia of Molecular Pharmacology (v. 1). Springer. p. 660. ISBN 978-3-540-38916-3. Retrieved 2015-01-01.