7766-38-3

Basic information

• Product Name: N-(4-nitrophenyl)acrylamide
• Synonyms: N-(4-nitrophenyl)acrylamide;2-Propenamide, N-(4-nitrophenyl)-;Ai3-61974;Einecs 231-861-2;N-(4-nitrophenyl)prop-2-enamide
• CAS NO: 7766-38-3
• Molecular Formula: C₉H₈N₂O₃
• Molecular Weight: 192.17142
• EINECS: 231-861-2
• Mol File: 7766-38-3.mol

Chemical Properties

• Boiling Point: 407.7°C at 760 mmHg
• Flash Point: 200.4°C
• Appearance: /
• Density: 1.316g/cm³
• Vapor Pressure: 7.37E-07mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: N-(4-nitrophenyl)acrylamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-nitrophenyl)acrylamide(7766-38-3)
• EPA Substance Registry System: N-(4-nitrophenyl)acrylamide(7766-38-3)

Safety Data

• Hazardous Substances Data: 7766-38-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H8N2O3/c1-2-9(12)10-7-3-5-8(6-4-7)11(13)14/h2-6H,1H2,(H,10,12)

Upstream product

• 100-01-6 4-nitro-aniline 
• 79-10-7 acrylic acid 
• 100-25-4 para-dinitrobenzene 
• 625-36-5 2-chloropropionyl chloride 
• 814-68-6 acryloyl chloride 
• 100-28-7 4-Nitrophenyl isocyanate 

Downstream Products

• 851651-84-8 3-(4-methylpiperazin-1-yl)-N-(4-nitrophenyl)propanamide 
• 7530-31-6 N-(4-Amino-phenyl)-acrylamide 
• 1357381-90-8 pyrrolidine-1-carboxylic acid (4-acryloylaminophenyl)-amide 
• 135036-42-9 N-[4-[(Methylsulfonyl)amino]phenyl]-1-phenyl-4-(phenylmethyl)-2-piperazinecarboxamide 
• 135036-40-7 N-<4-<(methylsulfonyl)amino>phenyl>-4-phenyl-1-(phenylmethyl)-2-piperazinecarboxamide 
• 135063-15-9 N-(4-nitrophenyl)-1-phenyl-4-(phenylmethyl)-2-piperazinecarboxamide 
• 135036-43-0 N-[4-[[[1-Phenyl-4-(phenylmethyl)piperazin-2-yl]methyl]amino]phenyl]methanesulfonamide 
• 135036-39-4 N-(4-nitrophenyl)-4-phenyl-1-(phenylmethyl)-2-piperazinecarboxamide 
• 135036-41-8 N-<<<<4-phenyl-1-(phenylmethyl)piperazin-2-yl>methyl>amino>phenyl>methanesulfonamide 

Relevant articles and documents

Synthesis and antiallergic activity of N-(pyridin-2-yl)-3-(piperazin-1-yl) propanamides

A series of 6 new N-(pyridin-2-yl)-3-(piperazin-1-yl)propanamides were synthesized from the corresponding N-pyridinylpropenamides to determine potential antiallergic activity as assayed in vivo by the passive cutaneous anaphylaxis test. The IC50 of compound 12 after oral administration was comparable to that of oxatomide.

Silyl Radical-Mediated Activation of Sulfamoyl Chlorides Enables Direct Access to Aliphatic Sulfonamides from Alkenes

Single electron reduction is more challenging for sulfamoyl chlorides than sulfonyl chlorides. However, sulfamoyl and sulfonyl chlorides can be easily activated by Cl-atom abstraction by a silyl radical with similar rates. This latter mode of activation was therefore selected to access aliphatic sulfonamides, applying a single-step hydrosulfamoylation using inexpensive olefins, tris(trimethylsilyl)silane, and photocatalyst Eosin Y. This late-stage functionalization protocol generates molecules as complex as sulfonamide-containing cyclobutyl-spirooxindoles for direct use in medicinal chemistry.

Disulfide Promoted C?P Bond Cleavage of Phosphoramide: “P” Surrogates to Synthesize Phosphonates and Phosphinates

A metal-free C?P bond cleavage reaction is described herein. Phosphoramides, a phosphine source, can react with alcohols to produce phosphonate and phosphinate derivatives in the presence of a disulfide. P?H2, P-alkyl, and P,P-dialkyl phosphoramides can be used as substrates to obtain the corresponding pentavalent phosphine products. (Figure presented.).

Design, synthesis and structure-activity relationship of diaryl-ureas with novel isoxazol[3,4-b]pyridine-3-amino-structure as multi-target inhibitors against receptor tyrosine kinase

Inspired by that the multi-target inhibitors against receptor tyrosine kinases (RTKs) have significantly improved the effect of clinical treatment for cancer, and based on the chemical structure of Linifanib (ABT-869, Abbott), two series of diaryl-ureas with novel isoxazol[3,4-b]pyridine-3-amino-structure were designed and synthesized as multi-target inhibitors against RTKs. The preliminary biological evaluation showed that several compounds exhibited comparable potency with Linifanib. Compound S21 was identified as the most potent inhibitor against Fms-like tyrosine kinase 3 (FLT-3), kinase insert domain containing receptor (KDR) and platelet-derived growth factor receptor β (PDGFR-β) with its IC50 values were 4 nM, 3 nM and 8 nM respectively, it also showed potent inhibitory activities against several cancer cells.

PYRAZOLOPYRIMIDINE DERIVATIVES, PREPARATION METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION FOR USE IN PREVENTING OR TREATING CANCER, AUTOIMMUNE DISEASE AND BRAIN DISEASE CONTAINING THE SAME AS AN ACTIVE INGREDIENT

The present invention relates to a pyrazolopyrimidine derivative, a preparation method thereof and a pharmaceutical composition comprising the same as an active ingredient for the prevention or treatment of cancer, autoimmune disease and brain disease. The pyrazolopyrimidine derivative of the present invention exhibits excellent Bruton's tyrosine kinase inhibition activity, so that it can be effectively used as a pharmaceutical composition for the prevention or treatment of cancer, autoimmune disease and Parkinson's disease.

Synthesis of thermo- and photo-responsive polysiloxanes with tunable phase separation: Via aza-Michael addition

Two kinds of thermo- and photo-dual-responsive polysiloxanes (DRPSs) with functional pendent groups, N-isopropyl amides and azobenzene (Azo) or salicylideneaniline (SA), were synthesized through a facile, effective, and catalyst-free aza-Michael addition of poly(aminopropylmethyl-siloxane) with N-isopropyl acrylamide and N-azobenzene acrylamide or N-salicylaldehyde acrylamide. The chemical structrures of DRPSs were systematically characterized using FT-IR, H NMR and UV-Vis spectroscopy. The as-prepared DRPSs with lower Azo or SA contents exhibited lower critical solution temperature (LCST)-type phase transition in water, which is reversible and can be controlled by temperature and UV light. The effects of Azo and SA contents on the responsive properties of DRPSs are examined in detail. The LCST decreased with the increasing Azo or SA content. Once the content of Azo or SA reached up to 5.7% or 8.2%, respectively, DRPSs could not be dissolved in water even in an ice bath. Higher values of the LCST were measured after irradiation of the polymer solutions due to the higher polarity of cis-Azo and keto-SA conformation, induced by irradiation. The differences in cloud points between the irradiated and the non-irradiated DRPS aqueous solutions increased up to 3.4 °C and 9.8 °C when combined with 3.8% Azo and 5.8% SA units, respectively.

PYRIMIDINE DERIVATIVES AS KINASE INHIBITORS AND THEIR THERAPEUTICAL APPLICATIONS

The present invention provides kinase inhibitors with anti-proliferative activity comprising substituted pyrimidine derivatives and pharmaceutically-acceptable formulations thereof. In addition, the invention provides methods for making novel compounds and methods for using the compounds.

Systematic study of the glutathione (GSH) reactivity of N-arylacrylamides: 1. Effects of aryl substitution

Success in the design of targeted covalent inhibitors depends in part on a knowledge of the factors influencing electrophile reactivity. In an effort to further develop an understanding of structure-reactivity relationships among N-arylacrylamides, we determined glutathione (GSH) reaction rates for a family of N-arylacrylamides independently substituted at ortho-, meta-, and para-positions with 11 different groups common to inhibitor design. We find that substituent effects on reaction rates show a linear Hammett correlation for ortho-, meta-, and para-substitution. In addition, we note a correlation between 1H and 13C NMR chemical shifts of the acrylamide with GSH reaction rates, suggesting that NMR chemical shifts may be a convenient surrogate measure of relative acrylamide reactivity. Density functional theory calculations reveal a correlation between computed activation parameters and experimentally determined reaction rates, validating the use of such methodology for the screening of synthetic candidates in a prospective fashion.

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.

A fragment-based method to discover irreversible covalent inhibitors of cysteine proteases

A novel fragment-based drug discovery approach is reported which irreversibly tethers drug-like fragments to catalytic cysteines. We attached an electrophile to 100 fragments without significant alterations in the reactivity of the electrophile. A mass spectrometry assay discovered three nonpeptidic inhibitors of the cysteine protease papain. The identified compounds display the characteristics of irreversible inhibitors. The irreversible tethering system also displays specificity: the three identified papain inhibitors did not covalently react with UbcH7, USP08, or GST-tagged human rhinovirus 3C protease.