Chemistry:Quinoxalinedione

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Quinoxalinedione
Skeletal formula
Space-filling model of quinoxalinedione
Names
Preferred IUPAC name
1,4-Dihydroquinoxaline-2,3-dione
Identifiers
3D model (JSmol)
EC Number
  • 239-901-0
UNII
Properties
C8H6N2O2
Molar mass 162.15
Appearance white solid
Density 1.549 g/cm3
Melting point > 300 °C (572 °F; 573 K)
Hazards
GHS pictograms GHS05: CorrosiveGHS07: Harmful
GHS Signal word Warning
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
Tracking categories (test):

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]

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. 
  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. https://books.google.com/books?id=EnfRBQAAQBAJ&pg=PA142. Retrieved 2015-01-01. 
  4. Turski, L.; Schoepp, D.D.; Cavalheiro, E.A. (2001) (in it). Excitatory Amino Acids: Ten Years Later. Biomedical and health research. IOS Press. p. 38. ISBN 978-1-58603-072-8. https://books.google.com/books?id=SyjATUyCS2QC&pg=PA38. 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. https://books.google.com/books?id=fGe6NDIGQpsC&pg=PA660. 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.