1401223-20-8

Basic information

• Product Name: 2-(4-ethylphenoxy)-N-isopropyl-N-((3-pyridin-3-yl)-1,2,4-oxadiazol-5-yl)methylacetamide
• Synonyms: 2-(4-ethylphenoxy)-N-isopropyl-N-((3-pyridin-3-yl)-1,2,4-oxadiazol-5-yl)methylacetamide
• CAS NO: 1401223-20-8
• Molecular Weight: 380.447
• Mol File: 1401223-20-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-(4-ethylphenoxy)-N-isopropyl-N-((3-pyridin-3-yl)-1,2,4-oxadiazol-5-yl)methylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-ethylphenoxy)-N-isopropyl-N-((3-pyridin-3-yl)-1,2,4-oxadiazol-5-yl)methylacetamide(1401223-20-8)
• EPA Substance Registry System: 2-(4-ethylphenoxy)-N-isopropyl-N-((3-pyridin-3-yl)-1,2,4-oxadiazol-5-yl)methylacetamide(1401223-20-8)

Safety Data

• Hazardous Substances Data: 1401223-20-8(Hazardous Substances Data)

Upstream product

• 1184229-50-2 N-((3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)methyl)propan-2-amine 
• 167762-94-9 2-(4-ethylphenoxy)acetyl chloride 
• 15328-03-7 5-(chloromethyl)-3-(pyridin-3-yl)-1,2,4-oxadiazole 
• 123-07-9 4-Ethylphenol 
• 1401223-72-0 (Z)-N'-(2-chloroacetoxy)nicotinimidamide 
• 1594-58-7 (Z)-N'-hydroxy(pyridin-3-yl)methanimidamide 
• 100-54-9 pyridine-3-carbonitrile 
• 24431-27-4 2-(4-ethylphenoxy)acetic acid 
• 71475-45-1 ethyl 2-(4-ethylphenoxy)acetate 

Relevant articles and documents

Oxadiazole-isopropylamides as potent and noncovalent proteasome inhibitors

Screening of the 50 000 ChemBridge compound library led to the identification of the oxadiazole-isopropylamide 1 (PI-1833) which inhibited chymotrypsin-like (CT-L) activity (IC50 = 0.60 μM) with little effects on the other two major proteasome proteolytic activities, trypsin-like (T-L) and postglutamyl-peptide-hydrolysis-like (PGPH-L). LC-MS/MS and dialysis show that 1 is a noncovalent and rapidly reversible CT-L inhibitor. Focused library synthesis provided 11ad (PI-1840) with CT-L activity (IC50 = 27 nM). Detailed SAR studies indicate that the amide moiety and the two phenyl rings are sensitive toward modifications. Hydrophobic residues, such as propyl or butyl in the para position (not ortho or meta) of the A-ring and a m-pyridyl group as B-ring, significantly improve activity. Compound 11ad (IC50 = 0.37 μM) is more potent than 1 (IC50 = 3.5 μM) at inhibiting CT-L activity in intact MDA-MB-468 human breast cancer cells and inhibiting their survival. The activity of 11ad warrants further preclinical investigation of this class as noncovalent proteasome inhibitors.