Skip to Content
MilliporeSigma
All Photos(1)

Documents

SML2412

Sigma-Aldrich

EU1794-4

≥98% (HPLC)

Synonym(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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C16H19N3O4S2
CAS Number:
305373-14-2
Molecular Weight:
381.47
MDL number:
MFCD01831186
UNSPSC Code:
12352200

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

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

Biochem/physiol Actions

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).

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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)
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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service