144581-86-2

Basic information

• Product Name: 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE
• Synonyms: 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE
• CAS NO: 144581-86-2
• Molecular Formula: C₁₀H₁₂BrNO₂
• Molecular Weight: 258.11178
• Mol File: 144581-86-2.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE(144581-86-2)
• EPA Substance Registry System: 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE(144581-86-2)

Safety Data

• Hazardous Substances Data: 144581-86-2(Hazardous Substances Data)

Usage

General Description

2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE is a chemical compound with the molecular formula C10H12BrNO2. It is a derivative of acetamide and contains a bromine atom, a methoxy group, and a methyl group, as well as a phenyl ring. 2-BROMO-N-(4-METHOXY-PHENYL)-N-METHYL-ACETAMIDE is often used in organic synthesis and pharmaceutical research, and it may have potential applications in the development of new drugs and medical treatments. Its specific properties and potential uses may vary depending on the context and the specific research or development goals.

Upstream product

• 79-08-3 bromoacetic acid 
• 2393-23-9 4-methoxy-benzylamine 
• 22118-09-8 2-bromoacetyl chloride 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 1006617-93-1 methyl 4-[((3-chloro-2-methylphenyl)-{2-[(4-methoxybenzyl)amino]-2-oxoethyl}amino)sulfonyl]benzoate 
• 1393643-61-2 N-hydroxy-4-{[(4-methoxybenzylcarbamoylmethyl)amino]methyl}benzamide 
• 1426435-36-0 2-(3-chloro-benzenesulfinyl)-N-(4-methoxy-benzyl)-acetamide 
• 1426435-57-5 2-(3-chloro-phenylsulfanyl)-N-(4-methoxy-benzyl)-acetamide 
• 609794-80-1 N-(4-methoxybenzyl)-2-(4-nitrophenoxy)acetamide 
• 117471-50-8 N,N'-bis(p-methoxybenzyl)-α-aminoacetamide 

Relevant articles and documents

Synthesis of Peptoid-Based Class I-Selective Histone Deacetylase Inhibitors with Chemosensitizing Properties

There is increasing evidence that histone deacetylase (HDAC) inhibitors can (re)sensitize cancer cells for chemotherapeutics via "epigenetic priming". In this work, we describe the synthesis of a series of class I-selective HDAC inhibitors with 2-aminoanilides as zinc-binding groups. Several of the synthesized compounds revealed potent inhibition of the class I HDAC isoforms HDAC1, HDAC2, and/or HDAC3 and promising antiproliferative effects in the human ovarian cancer cell line A2780 and the human squamous carcinoma cell line Cal27. Selected compounds were investigated in a cellular model of platinum resistance. In particular, compound 2a revealed potent chemosensitizing properties and full reversal of cisplatin resistance in Cal27CisR cells. This effect is related to a synergistic increase in caspase 3/7 activation and induction of apoptosis. Thus, this work demonstrates that pan-HDAC inhibition or dual class I/class IIb inhibition is not required for full reversal of cisplatin resistance.

A new synthetic approach to the imidazo[1,5-: A] imidazole-2-one scaffold and effective functionalization through Suzuki-Miyaura cross coupling reactions

We report herein a synthetic pathway to new 7-bromo-1-(4-methoxybenzyl)-5-methyl-imidazo[1,5-a]imidazole-2-one. The synthetic potential of this scaffold was demonstrated by displacing bromine by Suzuki-Miyaura cross-coupling reactions. A large panel of bo

Synthesis and in Vitro Evaluation of Novel 5-Nitroindole Derivatives as c-Myc G-Quadruplex Binders with Anticancer Activity

Lead-optimization strategies for compounds targeting c-Myc G-quadruplex (G4) DNA are being pursued to develop anticancer drugs. Here, we investigate the structure-activity- relationship (SAR) of a newly synthesized series of molecules based on the pyrrolidine-substituted 5-nitro indole scaffold to target G4 DNA. Our synthesized series allows modulation of flexible elements with a structurally preserved scaffold. Biological and biophysical analyses illustrate that substituted 5-nitroindole scaffolds bind to the c-Myc promoter G-quadruplex. These compounds downregulate c-Myc expression and induce cell-cycle arrest in the sub-G1/G1 phase in cancer cells. They further increase the concentration of intracellular reactive oxygen species. NMR spectra show that three of the newly synthesized compounds interact with the terminal G-quartets (5′- and 3′-ends) in a 2 : 1 stoichiometry.

First Nondiscriminating Translocator Protein Ligands Produced from a Carbazole Scaffold

Development of neuroinflammation agents targeting the translocator protein (TSPO) has been hindered by a common single nucleotide polymorphism (A147T) at which TSPO ligands commonly lose affinity. To this end, carbazole acetamide scaffolds were synthesized and structure activity relationships elaborated to explore the requirements for high-affinity binding to both TSPO wild type (WT) and the polymorphic TSPO A147T. This study reports high binding affinity and nondiscriminating TSPO ligands.