77053-60-2

Basic information

• Product Name: methyl 2-bromo-2-(4-tert-butylphenyl)acetate
• Synonyms: methyl 2-bromo-2-(4-tert-butylphenyl)acetate
• CAS NO: 77053-60-2
• Molecular Weight: 285.181
• Mol File: 77053-60-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl 2-bromo-2-(4-tert-butylphenyl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-bromo-2-(4-tert-butylphenyl)acetate(77053-60-2)
• EPA Substance Registry System: methyl 2-bromo-2-(4-tert-butylphenyl)acetate(77053-60-2)

Safety Data

• Hazardous Substances Data: 77053-60-2(Hazardous Substances Data)

Upstream product

• 3549-23-3 methyl 2-(4-tert-butylphenyl)acetate 

Downstream Products

• 186026-06-2 methyl α-hexylthio-4-tert-butylphenylacetate 
• 1208861-72-6 tetraethylammonium S-[methoxycarbonyl-(4-tert-butylphenyl)methyl] thiosulfate 
• 86215-71-6 1-(4-(tert-butyl)phenyl)-3-azabicyclo[3.1.0]hexane 
• 77053-85-1 (1R,2S)-1-(4-tert-Butyl-phenyl)-cyclopropane-1,2-dicarboxylic acid 
• 77062-89-6 (1R,2S)-1-(4-tert-Butyl-phenyl)-cyclopropane-1,2-dicarboxylic acid dimethyl 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.

1-Aryl-3-azabicyclohexanes, a New Series of Nonnarcotic Analgesic Agents

A series of 1-aryl-3-azabicyclohexanes was synthesized by hydride reduction of 1-arylcyclopropanedicarboximides.Hydroxyphenyl analogues 20, 22, and 24 were prepared by EtSNa-DMF ether cleavage of the corresponding methoxyphenyl analogues 2m, 2n, and 23, respectively, with the secondary amines 20 and 22 going through the N-formyl intermediates 19 and 21.The p-ethoxy analogue 26 was obtained by O-ethylation of 19, followed by base hydrolysis of the amide 25.The greatest analgesic potency in mouse writhing and rat paw-pain assays was observed for para-substituted compounds.Bicifadine, 1-(4-methylphenyl)-3-azabicyclohexane (2b), was the most potent member of the series and is presently undergoing clinical trials in man.Analgesic activity of 2b is limited to the (+) enantiomer 2v, which has the 1R,5S absolute configuration as determined by single-crystal X-ray analysis.The N-methyl analogue (27d) of 2b showed significant analgesic potency, whereas the N-allyl (27a), N-(cyclopropylmethyl) (27b), and N-(n-hexyl) (27c) analogues were inactive.Bicifadine (2b) showed a nonnarcotic profile different from analogous azabicycloalkane and 3-phenylpyrrolidine analgesics.