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W105

Sigma-Aldrich

S(−)-Willardiine

solid

Synonym(s):

S(−)-α-Amino--3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinepropanoic acid

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About This Item

Empirical Formula (Hill Notation):
C7H9N3O4
CAS Number:
21416-43-3
Molecular Weight:
199.16
MDL number:
MFCD00153879
UNSPSC Code:
12352200
PubChem Substance ID:
24278009

form

solid

color

white

solubility

0.1 M NaOH: 7.2 mg/mL
DMSO: insoluble
H2O: insoluble
ethanol: insoluble

SMILES string

[H]C1=CN(C[C@H](N)C(O)=O)C(=O)NC1=O

Gene Information

human ... GRIA1(2890) , GRIA2(2891) , GRIA3(2892) , GRIA4(2893) , GRIK1(2897) , GRIK2(2898) , GRIK3(2899) , GRIK4(2900) , GRIK5(2901)

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Biochem/physiol Actions

AMPA/kainate glutamate receptor agonist.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Michael K Fenwick et al.
Journal of molecular biology, 378(3), 673-685 (2008-04-05)
Glutamate receptors mediate neuronal intercommunication in the central nervous system by coupling extracellular neurotransmitter-receptor interactions to ion channel conductivity. To gain insight into structural and dynamical factors that underlie this coupling, solution NMR experiments were performed on the bilobed ligand-binding
Ahmed H Ahmed et al.
Biochemistry, 48(18), 3894-3903 (2009-03-17)
Ionotropic glutamate receptors mediate the majority of vertebrate excitatory synaptic transmission. The development of selective antagonists for glutamate receptor subtypes is of interest in the treatment of a variety of neurological disorders. This study presents the crystal structure of the
Jeremy R Greenwood et al.
Neuropharmacology, 51(1), 52-59 (2006-04-25)
Three positional isomers (compounds 1, 2, and 3) of 1-uracilylalanine (willardiine) based on a 3-hydroxypyridazine 1-oxide scaffold with an alanine side-chain at positions 4 (1), 5 (2) or 6 (3) were tested for binding to recombinant homomeric AMPA receptor (AMPA-R)
Teruyuki Fukushima et al.
Neuroscience letters, 349(2), 107-110 (2003-08-30)
Heteromeric GluR6/KA-2 kainate receptor were expressed in HEK293 cells and an inhibition of willardiine-induced currents by cations was studied. Zinc was much more effective than Ca(2+), Ba(2+) and Mg(2+) at 235, 265 and 1382 fold increase in IC(50), respectively. The
D E Jane et al.
Journal of medicinal chemistry, 40(22), 3645-3650 (1997-11-14)
Both willardiine and azawillardiine analogs (18-28) have been reported to be potent and selective agonists for either AMPA or kainate receptors. We report here the novel synthesis and pharmacological characterization of a range of willardiine (18-23) and 6-azawillardiine (24-28) analogs
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