7507-32-6

Usage

Derivative of acetic acid

It is a modified form of acetic acid, with additional functional groups attached to the basic acetic acid structure.

Propyl group attachment

The compound contains a propyl group (a three-carbon chain) attached to a phenoxy group, which influences its chemical properties and applications.

Pharmaceutical and agricultural applications

2-(4-propylphenoxy)acetic acid is used in both pharmaceutical and agricultural industries for various purposes.

Herbicide

It serves as a herbicide, helping to control and prevent the growth of unwanted plants.

Plant growth regulator

The compound can also act as a plant growth regulator, influencing the growth and development of plants in a controlled manner.

Intermediate in organic synthesis

2-(4-propylphenoxy)acetic acid is used as an intermediate in the synthesis of various other organic compounds, contributing to the formation of different chemical products.

Environmental and health hazards

The compound has potential risks to both the environment and human health, necessitating careful handling and disposal procedures to minimize harm.

Cautious handling and disposal

Due to its potential hazards, it is essential to handle and dispose of 2-(4-propylphenoxy)acetic acid with caution, following appropriate safety guidelines and regulations.

InChI:InChI=1/C11H14O3/c1-2-3-9-4-6-10(7-5-9)14-8-11(12)13/h4-7H,2-3,8H2,1H3,(H,12,13)

Upstream product

• 645-56-7 4-n-Propylphenol 
• 79-11-8 chloroacetic acid 
• 108-95-2 phenol 
• 105-36-2 ethyl bromoacetate 
• 832740-24-6 (4-Propyl-phenoxy)-essigsaeure-ethylester 
• 1401223-55-9 tert-butyl 2-(4-propylphenoxy)acetate 

Downstream Products

• 1092299-88-1 (4-propylphenoxy)acetyl chloride 
• 1401223-34-4 N-isopropyl-2-(4-propylphenoxy)-N-((3-p-tolyl-1,2,4-oxadiazol-5-yl)methyl)acetamide 
• 1401223-33-3 N-isopropyl-2-(4-propylphenoxy)-N-((3-(pyrimidin-2-yl)-1,2,4-oxadiazol-5-yl)methyl)acetamide 
• 1401223-31-1 N-isopropyl-2-(4-propylphenoxy)-N-((3-(pyrazin-2-yl)-1,2,4-oxadiazol-5-yl)methyl)acetamide 
• 1401223-30-0 N-isopropyl-2-(4-propylphenoxy)-N-((3-(pyrimidin-5-yl)-1,2,4-oxadiazol-5-yl)methyl)acetamide 
• 1401223-22-0 PI-1840 

Relevant academic research and scientific papers

Triaryl compound and preparation method and pharmaceutical application thereof

The invention discloses a triaryl compound as shown in a formula I which is described in the specification, physiologically acceptable salt, a preparation method of the compound, a pharmaceutical preparation containing the compound, and application of the

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.

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.

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)