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SML3643

Sigma-Aldrich

EP2 antagonist C52

≥98% (HPLC)

Synonym(s):

4-((9-Chloro-7-(5-fluoro-1H-indol-1-yl)-2,3-dihydrobenzo[f ]-[1,4]oxazepin-4(5H)-yl)methyl)pyridin-2(1H)-one, 4-[[9-Chloro-7-(5-fluoro-1H-indol-1-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]methyl]-2(1H)-pyridinone, Benzoxazepine 52, C52, Compound 52, EP2 antagonist compound 52

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About This Item

Empirical Formula (Hill Notation):
C23H19ClFN3O2
CAS Number:
1799626-16-6
Molecular Weight:
423.87
UNSPSC Code:
12352200
NACRES:
NA.25

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (Warmed)

storage temp.

2-8°C

SMILES string

O=C1C=C(CN2CC3=CC(N4C=CC5=C4C=CC(F)=C5)=CC(Cl)=C3OCC2)C=CN1

Biochem/physiol Actions

Compound 52 (C52) is an orally active, brain-penetrant, highly potent and selective prostaglandin E2 (PGE2) receptor 2 (EP2) antagonist (h/r/m EP2 IC50 = 8/10/10 nM against PGE2 binding, IC50 = 5/3/4 nM against 10 nM PGE2-induced cellular cAMP) with ∼4000-fold selectivity over other EP receptors (hEP1/3/4 IC50 >30 μM against PGE2 binding; hCRTH2/DP/IP/TP IC50 >33 μM against LTD4-induced cellular Ca2+) and no CYP inhibitory potency. C52 reduces inflammatory neurodegeneration in a murine model of cerebral ischemia (10 mg/kg p.o. 4.5h & 24h post MCAO) and restores cognition in aged mice (10 mg/kg/d p.o.) by rejuvenating cellular bioenergetics in vivo.

Storage Class Code

11 - Combustible Solids

WGK

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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Qingkun Liu et al.
Proceedings of the National Academy of Sciences of the United States of America, 116(20), 10019-10024 (2019-05-01)
The inflammatory prostaglandin E2 (PGE2) EP2 receptor is a master suppressor of beneficial microglial function, and myeloid EP2 signaling ablation reduces pathology in models of inflammatory neurodegeneration. Here, we investigated the role of PGE2 EP2 signaling in a model of
Brian M Fox et al.
Journal of medicinal chemistry, 58(13), 5256-5273 (2015-06-11)
A high-throughput screen resulted in the discovery of benzoxazepine 1, an EP2 antagonist possessing low microsomal stability and potent CYP3A4 inhibition. Modular optimization of lead compound 1 resulted in the discovery of benzoxazepine 52, a molecule with single-digit nM binding
Paras S Minhas et al.
Nature, 590(7844), 122-128 (2021-01-22)
Ageing is characterized by the development of persistent pro-inflammatory responses that contribute to atherosclerosis, metabolic syndrome, cancer and frailty1-3. The ageing brain is also vulnerable to inflammation, as demonstrated by the high prevalence of age-associated cognitive decline and Alzheimer's disease4-6.

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