Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

GYKI 52466

From Wikipedia, the free encyclopedia
(Redirected fromGYKI-52,466)
GYKI 52466
Skeletal formula
Space-filling model of GYKI-52,466
Names
Preferred IUPAC name
4-(8-Methyl-2H,9H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)aniline
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.162.378Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C17H15N3O2/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11/h2-5,7-8H,6,9,18H2,1H3 ☒N
    Key: LFBZZHVSGAHQPP-UHFFFAOYSA-N ☒N
  • InChI=1/C17H15N3O2/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11/h2-5,7-8H,6,9,18H2,1H3
    Key: LFBZZHVSGAHQPP-UHFFFAOYAH
  • CC1=NN=C(C2=CC3=C(C=C2C1)OCO3)C4=CC=C(C=C4)N
Properties
C17H15N3O2
Molar mass293.326 g·mol−1
AppearanceYellow solid (HCl salt)
Density1.393 g/cm3
>10 mg/mL (HCl salt)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

GYKI 52466 is a 2,3-benzodiazepine that acts as an ionotropicglutamatereceptor antagonist, which is a non-competitiveAMPA receptorantagonist (IC50 values are 10-20, ~ 450 and >> 50 μM for AMPA-, kainate- and NMDA-induced responses respectively), orally-activeanticonvulsant, andskeletal musclerelaxant.[1][2][3][4] Unlike conventional 1,4-benzodiazepines, GYKI 52466 and related 2,3-benzodiazepines do not act onGABAA receptors.[5] Like other AMPA receptor antagonists, GYKI 52466 has anticonvulsant andneuroprotective properties.[6]

CNS review:[7]

See also

[edit]

References

[edit]
  1. ^Donevan, S.D; Rogawski, M.A (1998). "Allosteric regulation of α-amino-3-hydroxy-5-methyl-4-isoxazole-propionate receptors by thiocyanate and cyclothiazide at a common modulatory site distinct from that of 2,3-benzodiazepines".Neuroscience.87 (3):615–629.doi:10.1016/s0306-4522(98)00109-2.PMID 9758228.S2CID 14817743.
  2. ^Donevan, Sean D.; Rogawski, Michael A. (1993). "GYKI 52466, a 2,3-benzodiazepine, is a highly selective, noncompetitive antagonist of AMPA/Kainate receptor responses".Neuron.10 (1):51–59.doi:10.1016/0896-6273(93)90241-i.PMID 7678966.S2CID 16011527.
  3. ^Tarnawa, István; Farkas, Sándor; Berzsenyi, Pál; Pataki, Ágnes; Andrási, Ferenc (1989). "Electrophysiological studies with a 2,3-benzodiazepine muscle relaxant: GYKI 52466".European Journal of Pharmacology.167 (2):193–199.doi:10.1016/0014-2999(89)90579-7.PMID 2574112.
  4. ^Rzeski, W.; Turski, L.; Ikonomidou, C. (2001)."Glutamate antagonists limit tumor growth".Proceedings of the National Academy of Sciences.98 (11):6372–6377.doi:10.1073/pnas.091113598.PMC 33475.PMID 11331750.
  5. ^Paternain, Ana V.; Morales, Miguel; Lerma, Juan (1995)."Selective antagonism of AMPA receptors unmasks kainate receptor-mediated responses in hippocampal neurons".Neuron.14 (1):185–189.doi:10.1016/0896-6273(95)90253-8.PMID 7826635.S2CID 6037517.
  6. ^Szabados, Tamás; Gigler, Gábor; Gacsályi, István; Gyertyán, István; Lévay, György (2001). "Comparison of anticonvulsive and acute neuroprotective activity of three 2,3-benzodiazepine compounds, GYKI 52466, GYKI 53405, and GYKI 53655".Brain Research Bulletin.55 (3):387–391.doi:10.1016/s0361-9230(01)00516-0.PMID 11489346.S2CID 23142293.
  7. ^Vizi, E. S., Mike, A., Tarnawa, I. (March 1996). "2,3-Benzodiazepines (GYKI 52466 and Analogs): Negative Allosteric Modulators of AMPA Receptors".CNS Drug Reviews.2 (1):91–126.doi:10.1111/j.1527-3458.1996.tb00292.x.
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
1,4-Benzodiazepines
1,5-Benzodiazepines
2,3-Benzodiazepines*
Triazolobenzodiazepines
Imidazobenzodiazepines
Oxazolobenzodiazepines
Thienodiazepines
Thienotriazolodiazepines
Thienobenzodiazepines*
Pyridodiazepines
Pyridotriazolodiazepines
Pyrazolodiazepines
Pyrrolodiazepines
Tetrahydroisoquinobenzodiazepines
Pyrrolobenzodiazepines*
Benzodiazepine prodrugs
* atypical activity profile (notGABAA receptor ligands)
Retrieved from "https://en.wikipedia.org/w/index.php?title=GYKI_52466&oldid=1315190428"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2025 Movatter.jp