70875-53-5

Usage

Also known as

N-(4-Methoxybenzyl)acrylamide

Physical state

Yellow solid at room temperature

Main use

Manufacture of pharmaceuticals and organic compounds

Classification

Acrylamide derivative

Properties

Anti-inflammatory and analgesic

Toxicity

Low

Potential use

Drug development and medical applications

Upstream product

• 2364-76-3 3-chloro-propionic acid-(4-methoxy-benzylamide) 
• 2393-23-9 4-methoxy-benzylamine 
• 814-68-6 acryloyl chloride 
• 107-13-1 acrylonitrile 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 185259-85-2 GR 46611 
• 619-73-8 4-nitrobenzyl chloride 
• 62-23-7 4-nitro-benzoic acid 

Relevant academic research and scientific papers

Reactivity of secondary N-alkyl acrylamides in Morita–Baylis–Hillman reactions

The Morita–Baylis–Hillman (MBH) reaction of secondary N-alkyl acrylamides, discarded up to now from investigations of the scope of activated alkenes, was studied. Optimization of the reaction conditions revealed that a balance must be found between activation of the MBH coupling reaction and that of the undesired competitive aldehyde Cannizzaro reaction. Using 3-Hydroxyquinuclidine (3-HQD) in a 1:1 water-2-MeTHF mixture provides the appropriate conditions that were applicable to a wide range of diversely substituted secondary N-alkyl acrylamides and aromatic aldehydes, giving rise to novel amide-containing MBH adducts under mild and clean conditions.

Predicting Monomers for Use in Polymerization-Induced Self-Assembly

We report an in silico method to predict monomers suitable for use in polymerization-induced self-assembly (PISA). By calculating the dependence of LogPoct /surface area (SA) on the length of the growing polymer chain, the change in hydrophobicity during polymerization was determined. This allowed for evaluation of the capability of a monomer to polymerize to form self-assembled structures during chain extension. Using this method, we identified five new monomers for use in aqueous PISA via reversible addition-fragmentation chain transfer (RAFT) polymerization, and confirmed that these all successfully underwent PISA to produce nanostructures of various morphologies. The results obtained using this method correlated well with and predicted the differences in morphology obtained from the PISA of block copolymers of similar molecular weight but different chemical structures. Thus, we propose this method can be utilized for the discovery of new monomers for PISA and also the prediction of their self-assembly behavior.

Chemoproteomics-enabled covalent ligand screen reveals a cysteine hotspot in reticulon 4 that impairs ER morphology and cancer pathogenicity

Chemical genetics has arisen as a powerful approach for identifying novel anti-cancer agents. However, a major bottleneck of this approach is identifying the targets of lead compounds that arise from screens. Here, we coupled the synthesis and screening of fragment-based cysteine-reactive covalent ligands with activity-based protein profiling (ABPP) chemoproteomic approaches to identify compounds that impair colorectal cancer pathogenicity and map the druggable hotspots targeted by these hits. Through this coupled approach, we discovered a cysteine-reactive acrylamide DKM 3-30 that significantly impaired colorectal cancer cell pathogenicity through targeting C1101 on reticulon 4 (RTN4). While little is known about the role of RTN4 in colorectal cancer, this protein has been established as a critical mediator of endoplasmic reticulum tubular network formation. We show here that covalent modification of C1101 on RTN4 by DKM 3-30 or genetic knockdown of RTN4 impairs endoplasmic reticulum and nuclear envelope morphology as well as colorectal cancer pathogenicity. We thus put forth RTN4 as a potential novel colorectal cancer therapeutic target and reveal a unique druggable hotspot within RTN4 that can be targeted by covalent ligands to impair colorectal cancer pathogenicity. Our results underscore the utility of coupling the screening of fragment-based covalent ligands with isoTOP-ABPP platforms for mining the proteome for novel druggable nodes that can be targeted for cancer therapy.

C3-CARBON LINKED GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN DEGRADATION

This invention provides Degronimers that have carbon-linked E3 Ubiquitin Ligase targeting moieties (Degrons), which can be linked to a targeting ligand for a protein that has been selected for in vivo degradation, and methods of use and compositions thereof as well as methods for their preparation.

(P2O5/SiO2): a useful heterogeneous alternative for the Ritter reaction

Tertiary alcohols as well as primary and secondary benzylic alcohols react efficiently with nitriles to give the corresponding amides in good to excellent yields in the presence of P2O5/SiO2 (60% w/w).

5-HT(1D) receptor agonist properties of novel 2-[5- [[(trifluoromethyl)sulfonyl]oxy]indolyl]ethylamines and their use as synthetic intermediates

2-[5-[[(Trifluoromethyl)sulfonyl]oxy]-1H-indol-3-yl]ethylamine (18), its N,N'-di-n-propyl (12), N,N-diethyl (13), and N,N-dimethyl (14) derivatives, and 4-[3-[2-(N,N-dimethylamino)ethyl]-1H-indol-3-yl]-N-(p- methoxybenzyl)acrylamide (GR46611, 19) were syn