27817-73-8

Basic information

• Product Name: N-[4-(methylthio)phenyl]acrylamide
• Synonyms: N-[4-(methylthio)phenyl]acrylamide;N-[4-(Methylthio)phenyl]propenamide
• CAS NO: 27817-73-8
• Molecular Formula: C₁₀H₁₁NOS
• Molecular Weight: 193.26544
• EINECS: 248-674-7
• Mol File: 27817-73-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 374.2°Cat760mmHg
• Flash Point: 180.1°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 8.46E-06mmHg at 25°C
• Refractive Index: 1.584
• PKA: 13.06±0.70(Predicted)
• CAS DataBase Reference: N-[4-(methylthio)phenyl]acrylamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4-(methylthio)phenyl]acrylamide(27817-73-8)
• EPA Substance Registry System: N-[4-(methylthio)phenyl]acrylamide(27817-73-8)

Safety Data

• Hazardous Substances Data: 27817-73-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H11NOS/c1-3-10(12)11-8-4-6-9(13-2)7-5-8/h3-7H,1H2,2H3,(H,11,12)

Upstream product

• 814-68-6 acryloyl chloride 
• 104-96-1 4-methylsulfanylaniline 

Downstream Products

• 86524-09-6 N-(4-Methylsulfanyl-phenyl)-3-(4-pyridin-2-yl-piperazin-1-yl)-propionamide 

Relevant articles and documents

Synthesis of 4-Trifluoromethylated 1,3-Butadienes via Palladium Catalyzed Heck Reaction

1,3-Butadiene plays a key role in modern synthetic chemistry and biochemistry because it is a key intermediate in the synthesis of many drugs. A new and effective method for the synthesis of 4-trifluoromethylated 1,3-butadiene through the fluorinated Heck reaction catalyzed by Pd(0) is described. Without additives, 1-chloro-3,3,3-trifluoropropene (an inexpensive CF3 structural unit that is harmless to ozone) reacts with enamide to synthesize 4-trifluoromethylated 1,3-butadienes with good yield, high regioselectivity and chemical selectivity, and strong tolerance of substrate functional groups such as alkynes, aldehyde, and ester groups.

COMPOSITIONS AND METHODS FOR INHIBITING RETICULON 4

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

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.