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
3D model (JSmol)
ECHA InfoCard 100.036.259
EC Number
  • 239-901-0
PubChem CID
UNII
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:

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. Poulie, Christian B. M.; Bunch, Lennart (2013). "Heterocycles as Nonclassical Bioisosteres of α-Amino Acids". ChemMedChem. 8 (2): 205–215. doi:10.1002/cmdc.201200436. PMID 23322633. S2CID 38623973.
  2. 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
  3. 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.
  4. 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.
  5. Offermanns, S.; Rosenthal, W. (2008). Encyclopedia of Molecular Pharmacology. Encyclopedia of Molecular Pharmacology. Springer. p. 660. ISBN 978-3-540-38916-3. Retrieved 2015-01-01.
  6. Dudić, Adela; Reiner, Andreas (2019). "Quinoxalinedione deprotonation is important for glutamate receptor binding". Biological Chemistry. 400 (7): 927–938. doi:10.1515/hsz-2018-0464. PMID 30903748.
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