:Quinoxalinedione
{{Chembox
| ImageFile = Quinoxalinedione.svg
| ImageSize = 175
| ImageAlt = Skeletal formula
| ImageFile1 = Quinoxalinedione molecule spacefill.png
| ImageSize1 = 175
| ImageAlt1 = Space-filling model of quinoxalinedione
| PIN = 1,4-Dihydroquinoxaline-2,3-dione
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 15804-19-0
| CASNo_Ref = {{cascite|correct|CAS}}
| EINECS = 239-901-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = APO55IZ9E1
| PubChem = 11469229
| StdInChI=1S/C8H4N2O2/c11-7-8(12)10-6-4-2-1-3-5(6)9-7/h1-4H
| StdInChIKey = SEPKUNXLGWMPHL-UHFFFAOYSA-N
| SMILES = C1=CC2=NC(=O)C(=O)N=C2C=C1
}}
|Section2={{Chembox Properties
| Formula = C8H6N2O2
| MolarMass = 162.15
| Appearance = white solid
| Density = 1.549 g/cm3
| MeltingPt = >
| MeltingPtC = 300
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS05}}{{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|315|318|319|335}}
| PPhrases = {{P-phrases|}}
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
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.{{cite journal |doi=10.1002/cmdc.201200436|title=Heterocycles as Nonclassical Bioisosteres of α-Amino Acids|year=2013|last1=Poulie|first1=Christian B. M.|last2=Bunch|first2=Lennart|journal=ChemMedChem|volume=8|issue=2|pages=205–215|pmid=23322633|s2cid=38623973}}
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.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}} 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.{{cite book|last=Ashley|first=M.J.|title=Traumatic Brain Injury: Rehabilitation, Treatment, and Case Management, Third Edition|publisher=CRC Press|year=2010|isbn=978-1-4398-4982-8|url=https://books.google.com/books?id=EnfRBQAAQBAJ&pg=PA142|access-date=2015-01-01|page=142}}{{cite book|last1=Turski|first1=L.|last2=Schoepp|first2=D.D.|last3=Cavalheiro|first3=E.A.|title=Excitatory Amino Acids: Ten Years Later|publisher=IOS Press|series=Biomedical and health research|year=2001|isbn=978-1-58603-072-8|url=https://books.google.com/books?id=SyjATUyCS2QC&pg=PA38|language=it|access-date=2015-01-01|page=38}}{{cite book|last1=Offermanns|first1=S.|last2=Rosenthal|first2=W.|title=Encyclopedia of Molecular Pharmacology|publisher=Springer|series=Encyclopedia of Molecular Pharmacology|issue=v. 1|year=2008|isbn=978-3-540-38916-3|url=https://books.google.com/books?id=fGe6NDIGQpsC&pg=PA660|access-date=2015-01-01|page=660}}{{Cite journal|last1=Dudić|first1=Adela|last2=Reiner|first2=Andreas|date=2019|title=Quinoxalinedione deprotonation is important for glutamate receptor binding|journal=Biological Chemistry|volume=400|issue=7|pages=927–938|doi=10.1515/hsz-2018-0464|pmid=30903748|doi-access=free}} Examples include the following:
- ACEA-1011
- Becampanel
- CNQX
- DNQX
- Fanapanel (MPQX)
- Licostinel (ACEA-1021)
- NBQX
- PNQX
- YM90K
- Zonampanel
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
{{Reflist|2}}
{{Ionotropic glutamate receptor modulators}}