50612-99-2

Basic information

• Product Name: Methyl 2-broMo-2-(4-Methoxyphenyl)acetate
• Synonyms: Methyl 2-broMo-2-(4-Methoxyphenyl)acetate
• CAS NO: 50612-99-2
• Molecular Formula: C₁₀H₁₁BrO₃
• Molecular Weight: 259.09654
• Mol File: 50612-99-2.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 119-136 °C(Press: 0.3-0.5 Torr)
• Appearance: /
• Density: 1.438±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Methyl 2-broMo-2-(4-Methoxyphenyl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-broMo-2-(4-Methoxyphenyl)acetate(50612-99-2)
• EPA Substance Registry System: Methyl 2-broMo-2-(4-Methoxyphenyl)acetate(50612-99-2)

Safety Data

• Hazardous Substances Data: 50612-99-2(Hazardous Substances Data)

Usage

Description

Methyl 2-Bromo-2-(4-Methoxyphenyl)acetate is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceuticals. It is characterized by its unique molecular structure, which includes a bromo and methoxyphenyl group attached to an acetate moiety. Methyl 2-broMo-2-(4-Methoxyphenyl)acetate plays a significant role in the development of medications targeting specific health conditions.

Uses

Used in Pharmaceutical Industry:
Methyl 2-Bromo-2-(4-Methoxyphenyl)acetate is used as an intermediate in the synthesis of Ambucetamide (A575935) for its role in creating an effective antispasmodic medication. Ambucetamide is particularly effective in providing relief from menstrual pain, making it a valuable compound in the development of treatments for dysmenorrhea.

Upstream product

• 67-56-1 methanol 
• 17478-44-3 α-bromo-4-methoxyphenylacetic acid 
• 104-01-8 4-Methoxyphenylacetic acid 
• 23786-14-3 4-methoxy-phenyl acetic acid methyl ester 

Downstream Products

• 53119-84-9 (4-Methoxy-phenyl)-[methyl-(toluene-4-sulfonyl)-amino]-acetic acid methyl ester 
• 113791-16-5 (S)-(4-Methoxy-phenyl)-((S)-2-oxo-3-phenylacetylamino-azetidin-1-yl)-acetic acid methyl ester 
• 113791-15-4 methyl D-2-(3-phenylacetamido-2-oxo-1-azetidinyl)-2-(4-methoxyphenyl)acetate 
• 140379-87-9 2-mercapto-2-(4-methoxyphenyl)acetic acid 
• 59845-69-1 methyl α-methoxy(4-methoxyphenyl)acetate 
• 682356-51-0 [5-methoxy-2-(4-methoxy-phenyl)-1,3-dioxo-indan-2-yl]-(4-methoxy-phenyl)-acetic acid methyl ester 
• 551929-13-6 (4-methoxy-phenyl)-[2-(4-methoxy-phenyl)-1,3-dioxo-indan-2-yl]-acetic acid methyl ester 
• 32191-55-2 (4-Methoxy-phenyl)-m-tolyloxy-acetic acid methyl ester 
• 32191-59-6 (3-Methoxy-phenoxy)-(4-methoxy-phenyl)-acetic acid methyl ester 

Relevant articles and documents

Discovery of 2-oxy-2-phenylacetic acid substituted naphthalene sulfonamide derivatives as potent KEAP1-NRF2 protein-protein interaction inhibitors for inflammatory conditions

Nuclear factor erythroid 2-related factor 2 (NRF2) is a pleiotropic transcription factor which regulates the constitutive and inducible transcription of a wide array of genes and confers protection against a variety of pathologies. Directly disrupting Kelch-like ECH-associated protein 1 (KEAP1)-NRF2 protein-protein interaction (PPI) has been explored as a promising strategy to activate NRF2. We reported here the first identification of a series of 2-oxy-2-phenylacetic acid substituted naphthalene sulfonamide derivatives as potent KEAP1-NRF2 inhibitors. Our efforts led to the potent small molecule KEAP1-NRF2 inhibitor, 20c, which exhibited a Kd of 24 nM to KEAP1 and an IC50 of 75 nM in disrupting KEAP1-NRF2 interaction. Subsequent biological studies provided consistent evidence across mouse macrophage cell-based and in vivo models that 20c induced NRF2 target gene expression and enhanced downstream antioxidant and anti-inflammatory activities. Our study not only demonstrated that small molecule KEAP1-NRF2 PPI inhibitors can be potential preventive and therapeutic agents for diseases and conditions involving oxidative stress and inflammation but also enriched the chemical diversity of the KEAP1-NRF2 inhibitors.

Structure-activity relationships study of neolamellarin A and its analogues as hypoxia inducible factor-1 (HIF-1) inhibitors

The novel marine pyrrole alkaloid neolamellarin A derived from sponge has been shown to inhibit hypoxia-induced HIF-1 activity. In this work, we designed and synthesized neolamellarin A and its series of derivatives by a convergent synthetic strategy. The HIF-1 inhibitory activity and cytotoxicity of these compounds were evaluated in Hela cells by dual-luciferase reporter gene assay and MTT assay, respectively. The results showed that neolamellarin A 1 (IC50 = 10.8 ± 1.0 μM) and derivative 2b (IC50 = 11.9 ± 3.6 μM) had the best HIF-1 inhibitory activity and low cytotoxicity. Our SAR research focused on the effects of key regions aliphatic carbon chain length, aromatic ring substituents and C-7 substituent on biological activity, providing a basis for the subsequent research on the development of novel pyrrole alkaloids as HIF-1 inhibitors and design of small molecule probes for target protein identification.

Development and evaluation of ST-1829 based on 5-benzylidene-2-phenylthiazolones as promising agent for anti-leukotriene therapy

Different inflammatory diseases and allergic reactions are mediated by leukotrienes, which arise from the oxygenation of arachidonic acid catalyzed by 5-lipoxygenase (5-LO). One promising approach for an effective anti-leukotriene therapy is the inhibition of this key enzyme. This study presents the synthesis and development of a potent and direct 5-LO inhibitor based on the well characterized 5-benzylidene-2-phenylthiazolone C06, whose further pharmacological investigation was precluded due to its low solubility. Through optimization of C06, evaluation of structure-activity relationships including profound assessment of the thiazolone core and consideration of the solubility, the 5-benzyl-2-phenyl-4-hydroxythiazoles represented by 46 (ST-1829, 5-(4-chlorobenzyl)-2-p-tolylthiazol-4-ol) were developed. Compound 46 showed an improved 5-LO inhibitory activity in cell-based (ICinf50/inf values 0.141/4M) and cell-free assays (ICinf50/inf values 0.03 1/4M) as well as a prominent enhanced solubility. Furthermore, it kept its promising inhibitory potency in the presence of blood serum, excluding excessive binding to serum proteins. These facts combined with the non-cytotoxic profile mark a major step towards an effective anti-inflammatory therapy.