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SML2412

Sigma-Aldrich

EU1794-4

≥98% (HPLC)

Synonyme(s) :

2-[[(2-Amino-4,5-dihydro-4-oxo-5-thiazolyl)acetyl]amino]-4,5,6,7-tetrahydro-1-benzo[b]thiophene-3-carboxylic acid ethyl ester, 2-[[(2-Imino-4-oxo-1,3-thiazolidin-5-yl)acetyl]amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid ethyl ester, EU 1794-4, Ethyl 2-(2-(2-imino-4-oxothiazolidin-5-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

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About This Item

Formule empirique (notation de Hill):
C16H19N3O4S2
Numéro CAS:
305373-14-2
Poids moléculaire :
381.47
Numéro MDL:
MFCD01831186
Code UNSPSC :
12352200

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

O=C(OCC)C1=C(SC2=C1CCCC2)NC(CC3SC(NC3=O)=N)=O

Actions biochimiques/physiologiques

EU1794-4 consists of an ethyl ester and lacks a methyl substituent on the tetrahydrobenzothiophene core.
EU1794-4 is an N-methyl-d-aspartate (NMDA) receptor (NMDAR) allosteric modulator that prevents large degree receptor activation in the presence of high level Glu/Gly (IC50/Emax = 2.2 μM/32%/GluN2A, 2.6 μM/67%/GluN2B, 0.42 μM/52%/GluN2C, 0.36 μM/51%/GluN2D with Glu/Gly = ECmax = 100/30 μM using xenopus oocytes co-expressing rat GluN1 and respective GluN2 subtype), while augmenting receptor activation at low level Glu/Gly (EC50/Emax = 3.9 μM/500%/GluN2A, 4.3 μM/210%/GluN2B, 15 μM/220%/GluN2C with Glu/Gly = 1/0.3 μM; 14 μM/540%/GluN2D with Glu/Gly = 300/9 nM).

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Brooke M Katzman et al.
Bioorganic & medicinal chemistry letters, 25(23), 5583-5588 (2015-11-04)
NMDA receptors mediate a slow Ca(2+)-permeable component of excitatory synaptic transmission, and are involved in numerous normal brain functions including learning and memory. NMDA receptor over-activation can lead to cell death and abnormal excitation in ischemia associated with stroke, traumatic
An NMDAR positive and negative allosteric modulator series share a binding site and are interconverted by methyl groups
Perszyk R, et al.
eLife, 7, e34711-e34711 (2018)
Mengxiao Shi et al.
Bioorganic & medicinal chemistry letters, 19(22), 6337-6339 (2009-10-13)
Secreted frizzled related protein-1 (sFRP-1) inhibitors have the potential to be used for the treatment of osteoporosis or other bone related disorders, since the level of sFRP-1 affects osteoblast apoptosis and proliferation. From high throughput screening, we have identified a
Riley Perszyk et al.
eLife, 7 (2018-05-25)
N-methyl-d-aspartate receptors (NMDARs) are an important receptor in the brain and have been implicated in multiple neurological disorders. Many non-selective NMDAR-targeting drugs are poorly tolerated, leading to efforts to target NMDAR subtypes to improve the therapeutic index. We describe here

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