2-[[[2-(4-ethylphenyl)-5-methyl-4-oxazolyl]methyl]thio]-N-(2-phenylethyl)acetamide

Product Name2-[[[2-(4-ethylphenyl)-5-methyl-4-oxazolyl]methyl]thio]-N-(2-phenylethyl)acetamide
CAS901751-47-1
MFC23H26N2O2S
MW394.53
EINECS
MOL File901751-47-1.mol

Chemical Properties

Density	1.150±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	DMSO: ≥5mg/mL
form	powder
pka	14.62±0.46(Predicted)
color	white to tan
InChI	InChI=1S/C23H26N2O2S/c1-3-18-9-11-20(12-10-18)23-25-21(17(2)27-23)15-28-16-22(26)24-14-13-19-7-5-4-6-8-19/h4-12H,3,13-16H2,1-2H3,(H,24,26)
InChIKey	QTDYVSIBWGVBKU-UHFFFAOYSA-N
SMILES	C(NCCC1=CC=CC=C1)(=O)CSCC1=C(C)OC(C2=CC=C(CC)C=C2)=N1

Safety Information

Hazard Codes	Xn
Risk Statements	22-37/38-41
Safety Statements	26-39
WGK Germany	3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Uses

iCRT3, is an inhibitor of both Wnt and β-catenin-responsive transcription (CRT).

Uses

iCRT3 has been used:

for β- catenin inhibition in dual luciferase assay
to inhibit β-catenin /TCF interactions and their transcriptional activity
as wingless/tailess (wnt) antagonist, to determine Wnt/β-catenin signaling is essential for PROX1-mediated regulation of forkhead box protein C2 (FOXC2)(3)catenin inhibition in dual luciferase assay
to inhibit β- catenin /TCF interactions and their transcriptional activity
as wingless/tailess (wnt) antagonist, to determine Wnt/β-catenin signaling is essential for PROX1-mediated regulation of forkhead box protein C2 (FOXC2)

General Description

iCRT3 is a small cell-permeable oxazole compound. It blocks cytokine secretion in lipopolysaccharide (LPS)-stimulated macrophages.

Biochem/physiol Actions

The key mediator of Wnt signaling is the transcriptional co-activator b-catenin. In the cytoplasm, b-catenin is tightly bound to a complex that includes Axin and GSK-3b. Stimulation causes b-catenin stabilization, translocation to the nucleus and association with TCF4 to initiate transcription of responsive genes, referred to as Catenin Responsive Transcription (CRT). Virtually all Wnt-associated cancers are the result of misregulated CRT. Three inhibitors of CRT (iCRT) were identified in a screen that employed RNAi based knockdown of Axin, which stimulates CRT without affecting upstream mechanisms such as GSK activity, transduction by disheveled / frizzled, etc. These compounds are potent inhibitors of CRT reporter genes, as well as endogenous gene targets. The compounds also disrupt b-catenin-TCF4 interaction in a dose dependent manner, and cause G0/G1 arrest in colon tumor lines.

in vivo

The tumor growth rates are markedly retarded by iCRT3 treatment. Consistently, the tumor-suppressive role of iCRT3 is accompanied with a reduction in Ki67 index, a proliferation marker^[1]. The IL-6 levels in the 10 mg/kg iCRT3 treatment group are 82.9% lower than those in the vehicle group. IL-1β levels are undetectable in the sham but reach 371 pg/mL in septic mice and are down by 30.2% and 53.2%, respectively, with 5 and 10 mg/kg iCRT3. With iCRT3 treatment at doses of 5 and 10 mg/kg, AST levels in these septic mice are 15.4% and 44.2% lower, respectively, than those in the vehicle-treated mice. After treatment with 10 mg/kg iCRT3, lung morphology is improved with much reduced microscopic deterioration, compare to the vehicle group. The number of apoptotic cells in the lung tissues of the iCRT3-treated mice is significantly reduced by 92.7% in comparison with the vehicle group^[3].

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