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5.04535

Sigma-Aldrich

QNZ46

Synonym(s):

QNZ46, NMDA Antagonist VIII, 4-[6-Methoxy-2-[(1E)-2-(3-nitrophenyl)ethenyl]-4-oxo-3(4H)-quinazolinyl]-Benzoic acid

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About This Item

Empirical Formula (Hill Notation):
C24H17N3O6
CAS Number:
1237744-13-6
Molecular Weight:
443.41
MDL number:
MFCD22666391
UNSPSC Code:
12352200

assay

≥98% (HPLC)

Quality Level

100

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

yellow

solubility

DMSO: 5 mg/mL

storage temp.

2-8°C

InChI

1S/C24H17N3O6/c1-33-19-10-11-21-20(14-19)23(28)26(17-8-6-16(7-9-17)24(29)30)22(25-21)12-5-15-3-2-4-18(13-15)27(31)32/h2-14H,1H3,(H,29,30)/b12-5+

InChI key

GNLVJIICVWDSNI-LFYBBSHMSA-N

General description

A noncompetitive and voltage-independent antagonist selective for NR2C/D containing NMDA receptors (IC50 = 6, 3, 229, and >300 µM for NR2C, NR2D, NR2A, and NR2B, respectively). Inhibition on NR2C/D containing NMDA receptors is glutamate-binding, but not glycine-binding, dependent. Represents a new class of noncompetitive subunit-selective NMDA receptor antagonists. With more than 100-fold selectivity for recombinant NMDA receptors over AMPA and kainate receptors.

Biochem/physiol Actions

Primary Target
NMDA receptors
Target IC50: 6, 3, 229, and >300 →M for NR2C, NR2D, NR2A, and NR2B, respectively.

Warning

Toxicity: Standard Handling (A)

Preparation Note

Slight warming is required for complete solubilization.

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Mayer, M., et al. 2013. Annu. Rev. Physiol.75, 1.

Hansen, K., 2011. J. Neurosci.9, 3650.

Mosley, C., et al. 2010. J. Med. Chem.53, 5476.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kasper B Hansen et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 31(10), 3650-3661 (2011-03-11)
NMDA receptors are ionotropic glutamate receptors that mediate excitatory synaptic transmission and have been implicated in several neurological diseases. We have evaluated the mechanism of action of a class of novel subunit-selective NMDA receptor antagonists, typified by (E)-4-(6-methoxy-2-(3-nitrostyryl)-4-oxoquinazolin-3(4H)-yl)-benzoic acid (QNZ46).
Cara A Mosley et al.
Journal of medicinal chemistry, 53(15), 5476-5490 (2010-08-06)
We describe a new class of subunit-selective antagonists of N-methyl D-aspartate (NMDA)-selective ionotropic glutamate receptors that contain the (E)-3-phenyl-2-styrylquinazolin-4(3H)-one backbone. The inhibition of recombinant NMDA receptor function induced by these quinazolin-4-one derivatives is noncompetitive and voltage-independent, suggesting that this family
Janesh Kumar et al.
Annual review of physiology, 75, 313-337 (2012-09-15)
X-ray crystal structures for the soluble amino-terminal and ligand-binding domains of glutamate receptor ion channels, combined with a 3.6-Å-resolution structure of the full-length AMPA receptor GluA2 homotetramer, provide unique insights into the mechanisms of the assembly and function of glutamate

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