Quinoxalinedione

Quinoxalinedione
Names
	Preferred IUPAC name 1,4-Dihydroquinoxaline-2,3-dione
Identifiers
CAS Number	15804-19-0 ;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.036.259
EC Number	239-901-0;
PubChem CID	11469229;
UNII	APO55IZ9E1 ;
CompTox Dashboard (EPA)	DTXSID9065946 ;
	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

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

^ 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.
^ 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
^ 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.
^ 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.
^ 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.
^ 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.

[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

[Ashley2010-3] 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.

[TurskSchoeppCavalheiro2001-4] 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.

[OffermannsRosenthal_2008-5] 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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