1257397-40-2

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl 2-(4-formyl-3-hydroxyphenyl)acetate is used as a key intermediate in the synthesis of various pharmaceuticals for its versatile reactivity and the presence of phenolic and aldehyde functional groups that can be exploited in the creation of new drug molecules.
Used in Organic Chemistry:
In the field of organic chemistry, methyl 2-(4-formyl-3-hydroxyphenyl)acetate is used as a reagent in the preparation of a wide range of organic compounds, taking advantage of its ability to undergo various chemical transformations.
Used in Medicinal Chemistry Research:
Methyl 2-(4-formyl-3-hydroxyphenyl)acetate is utilized as a subject of study in medicinal chemistry for its potential bioactivity, which includes antioxidant and anti-inflammatory properties attributed to its phenolic structure. This makes it a candidate for the development of new therapeutic agents.
Used in Antioxidant and Anti-Inflammatory Applications:
Due to its phenolic structure, methyl 2-(4-formyl-3-hydroxyphenyl)acetate is studied for its potential use as an antioxidant and anti-inflammatory agent, which could be beneficial in the treatment of various diseases and conditions where oxidative stress and inflammation are factors.

Upstream product

• 50-00-0 formaldehyd 
• 42058-59-3 3-hydroxy-benzeneacetic acid, methyl ester 

Downstream Products

• 1257397-68-4 methyl 2-(4-((4-fluorophenyl)(4-(trifluoromethyl)piperidin-1-yl)methyl)-3-hydroxyphenyl)acetate 
• 1257396-15-8 2-(6-(2-cyclohexyl-1-(4-(trifluoromethyl)piperidin-1-yl)ethyl)-4'-(trifluoromethyl)biphenyl-3-yl)acetic acid 
• 1257396-75-0 [6-{cyclohexyl[4-(trifluoromethyl)piperidin-1-yl]methyl}-4'-(trifluoromethyl)biphenyl-3-yl]acetic acid 
• 1257394-37-8 [4'-(trifluoromethyl)-6-{[4-(trifluoromethyl)piperidin-1-yl]methyl}biphenyl-3-yl]acetic acid 
• 1257397-82-2 methyl 2-(6-(2-cyclohexyl-1-(4-(trifluoromethyl)piperidin-1-yl)ethyl)-4'-(trifluoromethyl)biphenyl-3-yl)acetate 
• 1257397-81-1 methyl 2-(6-(1-bromo-2-cyclohexylethyl)-4'-(trifiuoromethyl)biphenyl-3-yl)acetate 
• 1257397-80-0 2-(6-(2-cyclohexyl-1-hydroxyethyl)-4'-(trifluoromethyl)biphenyl-3-yl)acetate 
• 1257394-81-2 {6-[(4-fluorophenyl)(4-methylpiperazin-1-yl)methyl]-4'-(trifluoromethyl)biphenyl-3-yl}acetic acid 

Relevant academic research and scientific papers

Discovery of BIIB042, a potent, selective, and orally bioavailable γ-secretase modulator

We have investigated a novel series of acid-derived γ-secretase modulators as a potential treatment of Alzheimer's disease. Optimization based on cellular potency and brain pharmacodynamics after oral dosing led to the discovery of 10a (BIIB042). Compound 10a is a potent γ-secretase modulator, which lowered Aβ42, increased Aβ38, but had little to no effect on Aβ40 levels both in vitro and in vivo. In addition, compound 10a did not affect Notch signaling in our in vitro assessment. Compound 10a demonstrated excellent pharmacokinetic parameters in multiple species. Oral administration of 10a significantly reduced brain Aβ42 levels in CF-1 mice and Fischer rats, as well as plasma Aβ42 levels in cynomolgus monkeys. Compound 10a was selected as a candidate for preclinical safety evaluation.

Discovery of 4-aminomethylphenylacetic acids as γ-secretase modulators via a scaffold design approach

Starting from literature examples of nonsteroidal anti-inflammatory drugs (NSAIDs)-type carboxylic acid γ-secretase modulators (GSMs) and using a scaffold design approach, we identified 4-aminomethylphenylacetic acid 4 with a desirable γ-secretase modulation profile. Scaffold optimization led to the discovery of a novel chemical series, represented by 6b, having improved brain penetration. Further SAR studies provided analog 6q that exhibited a good pharmacological profile. Oral administration of 6q significantly reduced brain Aβ42 levels in mice and rats.

CARBOXYLIC ACID-CONTAINING COMPOUNDS, DERIVATIVES THEREOF, AND RELATED METHODS OF USE

Compounds that modulate gamma secretase (e.g., alter the cleavage pattern of gamma secretase) are described herein. Also disclosed are pharmaceutical compositions, methods of modulating the activity of gamma secretase, and methods of treating Alzheimer's Disease using the compounds described herein.