94721-78-5

Basic information

• Product Name: Acetic acid, (4-pentylphenoxy)-
• CAS NO: 94721-78-5
• Molecular Formula: C13H18O3
• Molecular Weight: 222.284
• Mol File: 94721-78-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Acetic acid, (4-pentylphenoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, (4-pentylphenoxy)-(94721-78-5)
• EPA Substance Registry System: Acetic acid, (4-pentylphenoxy)-(94721-78-5)

Safety Data

• Hazardous Substances Data: 94721-78-5(Hazardous Substances Data)

Upstream product

• 1401223-57-1 tert-butyl 2-(4-pentylphenoxy)acetate 
• 14938-35-3 4-n-pentylphenol 
• 108-95-2 phenol 
• 110-62-3 pentanal 
• 79-08-3 bromoacetic acid 
• 79-11-8 chloroacetic acid 

Downstream Products

• 1401223-24-2 N-isopropyl-2-(4-pentylphenoxy)-N-(((3-pyridin-3-yl)-1,2,4-oxadiazol-5-yl)methyl)acetamide 
• 94721-77-4 p-cyanobiphenylyl p-pentylphenoxyacetate 
• 94721-76-3 p-cyanophenyl p-pentylphenoxyacetate 

Relevant articles and documents

Methyl 3-(3-(4-(2,4,4-Trimethylpentan-2-yl)phenoxy)-propanamido)benzoate as a Novel and Dual Malate Dehydrogenase (MDH) 1/2 Inhibitor Targeting Cancer Metabolism

Previously, we reported a hypoxia-inducible factor (HIF)-1 inhibitor LW6 containing an (aryloxyacetylamino)benzoic acid moiety inhibits malate dehydrogenase 2 (MDH2) using a chemical biology approach. Structure-activity relationship studies on a series of (aryloxyacetylamino)benzoic acids identified selective MDH1, MDH2, and dual inhibitors, which were used to study the relationship between MDH enzyme activity and HIF-1 inhibition. We hypothesized that dual inhibition of MDH1 and MDH2 might be a powerful approach to target cancer metabolism and selected methyl-3-(3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanamido)-benzoate (16c) as the most potent dual inhibitor. Kinetic studies revealed that compound 16c competitively inhibited MDH1 and MDH2. Compound 16c inhibited mitochondrial respiration and hypoxia-induced HIF-1α accumulation. In xenograft assays using HCT116 cells, compound 16c demonstrated significant in vivo antitumor efficacy. This finding provides concrete evidence that inhibition of both MDH1 and MDH2 may provide a valuable platform for developing novel therapeutics that target cancer metabolism and tumor growth.

PROTEASOME CHYMOTRYPSIN-LIKE INHIBITION USING PI-1833 ANALOGS

Focused library synthesis and medicinal chemistry on an oxadiazole- isopropylamide core proteasome inhibitor provided the lead compound that strongly inhibits CT-L activity. Structure activity relationship studies indicate the amide moiety and two phenyl rings are sensitive toward synthetic modifications. Only para-substitution in the A-ring was important to maintain potent CT-L inhibitory activity. Hydrophobic residues in the A-ring?s para-position and meta-pyridyl group at the B- ring significantly improved inhibition. The meta-pyridyl moiety improved cell permeability. The length of the aliphatic chain at the para position of the A-ring is critical with propyl yielding the most potent inhibitor, whereas shorter (i.e. ethyl, methyl or hydrogen) or longer (i.e. butyl, propyl and hexyl) chains demonstrating progressively less potency. Introduction of a stereogenic center next to the ether moiety (i.e. substitution of one of the hydrogens by methyl) demonstrated chiral discrimination in proteasome CT-L activity inhibition (the S-enantiomer was 35-40 fold more potent than the R-enantiomer)