51357-96-1

Usage

Physical appearance

White to off-white crystalline solid

Primary use

Monomer in the production of polymers and copolymers for industrial applications such as adhesives, coatings, and personal care products

Other uses

Studied for potential use in drug delivery systems due to biocompatibility and ability to self-assemble into nanostructures

Potential hazards

Identified as potential allergens and irritants, caution should be taken when working with this chemical

Upstream product

• 156-28-5 2-phenylethylamine hydrochloride 
• 814-68-6 acryloyl chloride 
• 64-04-0 phenethylamine 
• 70875-36-4 N-(β-phenethyl)-3-bromopropionamide 
• 306-20-7 3-chloro-N-(4-phenylethyl)propanamide 

Downstream Products

• 214064-41-2 17-(cyclopropylmethyl)-4,5α-epoxy-3,6β-dihydroxy-6,14-endoethenomorphinan-7α-(N-phenethyl)carboxamide 
• 1098101-09-7 (S,2E,4E)-7-methoxy-N-phenethyltetradeca-2,4-dienamide 
• 70875-36-4 N-(β-phenethyl)-3-bromopropionamide 

Relevant academic research and scientific papers

Photo-Enhanced Antimicrobial Activity of Polymers Containing an Embedded Photosensitiser

This work presents the synthesis of a novel photosensitive acrylate monomer for use as both a self-catalyst in the photoinduced electron/energy transfer–reversible addition fragmentation chain transfer (PET-RAFT) polymerisation process and a photosensitis

The mckenna reaction – avoiding side reactions in phosphonate deprotection

The McKenna reaction is a well-known and popular method for the efficient and mild synthesis of organophosphorus acids. Bromotrimethylsilane (BTMS) is the main reagent in this reaction, which transforms dialkyl phosphonate esters into bis(trimethylsilyl)esters, which are then easily converted into the target acids. However, the versatile character of the McKenna reaction is not always used to its full extent, due to formation of side products. Herein, demonstrated by using model examples we have not only analyzed the typical side processes accompanying the McKenna reaction, but also uncovered new ones. Further, we discovered that some commonly recommended precautions did not always circumvent the side reactions. The proposed results and recommendations may facilitate the synthesis of phosphonic acids.

COMPOSITONS AND METHODS FOR MODULATING UBA5

Disclosed herein, inter alia, are compositions and methods useful for inhibiting ubiquitin-like modifier activating enzyme 5.

COMPOSITIONS AND METHODS FOR MODULATING PPP2R1A

Disclosed herein, inter alia, are compositions and methods useful for modulating PPP2R1 A and for the treatment of cancer.

COMPOSITIONS AND METHODS FOR INHIBITING RETICULON 4

Disclosed herein, inter alia, are compositions and methods useful for inhibiting reticulon 4(RTN4).

Towards Sequence-Controlled Antimicrobial Polymers: Effect of Polymer Block Order on Antimicrobial Activity

Synthetic polymers have shown promise in combating multidrug-resistant bacteria. However, the biological effects of sequence control in synthetic antimicrobial polymers are currently not well understood. As such, we investigate the antimicrobial effects o

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.

Promiscuity and selectivity in covalent enzyme inhibition: A systematic study of electrophilic fragments

Covalent ligand-target interactions offer significant pharmacological advantages. However, off-target reactivity of the reactive groups, which usually have electrophilic properties, must be minimized, and the selectivity of irreversible inhibitors is a crucial requirement. We therefore performed a systematic study to determine the selectivity of several electrophilic groups that can be used as building blocks for covalently binding ligands. Six reactive groups with modulated electrophilicity were combined with 11 nonreactive moieties, resulting in a small combinatorial library of 72 fragment-like compounds. These compounds were screened against a group of 11 enzyme targets to assess their selectivity and their potential for promiscuous binding to proteins. The assay results showed a considerably lower degree of promiscuity than initially expected, even for those members of the screening collection that contain supposedly highly reactive electrophiles.

Synthesis of monoconjugated and multiply conjugated oligonucleotides by "click thiol" thiol-Michael-type additions and by combination with CuAAC "click huisgen"

Monoconjugated and multiply conjugated oligonucleotides were efficiently synthesized by starting from mono-thiohexyl- or tetra-thiohexyl-oligonucleotides and treatment with acrylamide derivatives (carbohydrates, ferrocene, biotin, fluorescent dyes, deoxyc

Rhodium catalysed conjugate addition of a chiral alkenyltrifluoroborate salt: The enantioselective synthesis of hermitamides A and B

The concise enantioselective synthesis of hermitamides A and B is presented utilising a rhodium catalysed conjugate addition reaction to introduce the side chain and chiral information in a single step via an alkenyltrifluoroborate salt.