40000-69-9

Usage

Chemical Class

Acrylamide

Functional Group

Contains a pyridinyl group

Uses

Commonly used in organic synthesis
Used as a building block in pharmaceutical production
Employed in polymer manufacture
Acts as a reagent in chemical reactions

Toxicity

Low acute toxicity
Prolonged exposure to high levels may cause irritation to:
Skin
Eyes
Respiratory tract
Potential mutagenic and teratogenic effects

Upstream product

• 504-29-0 2-aminopyridine 
• 814-68-6 acryloyl chloride 
• 625-36-5 2-chloropropionyl chloride 

Downstream Products

• 1412411-06-3 (E)-3-(7-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)-N-(pyridin-2-yl)acrylamide 

Relevant academic research and scientific papers

Molecular recognition by fluorescent imprinted polymers

New fluorescent imprinted polymers have been prepared for guest-host selectivity studies. Significant differences were found in the fluorescence response between the bound and unbound states.

Synthesis and Biological Activity of Acrylate Copolymers Containing 3-Oxo-N-allyl-1,2-benzisothiazole-3(2H)-carboxamide Monomer as a Marine Antifouling Coating

A type of grafted acrylate copolymer resins, containing 3-oxo-N-allyl-1,2-benzisothiazole-2(3H)-carboxamide monomer and heterocyclic monomers, was synthesized through the copolymeri- zation of methyl methacrylate (MMA) and butyl acrylate (BA) with functional monomers. The structures of the monomers and copolymers were validated by infrared (IR) and 1H nuclear magnetic resonance (NMR) spectroscopies. The inhibitory activities of the copolymers on algae, bacteria, and barnacle larvae were measured, and the antifouling potencies against marine macrofouling organisms were investigated. The results showed that the grafted resin had significant inhibitory effects on the growth of three marine algae (Isochrysis galbana, Nannochloropsisoculata, and Chlorella pyrenoidosa), and three bacteria (Vibrio coralliilyticus, Staphylococcus aureus,and Vibrio parahaemolyticus). The target copolymers also showed excellent inhibition of the survival of barnacle larvae. Additionally, the release rate of the antifoulant and the results of the marine field tests indicated that the grafted copolymers had outstanding antifouling potency against the attachment of marine macrofouling organisms.

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.).

Novel 5-arylcarbamoyl-2-methylisoxazolidin-3-yl-3-phosphonates as nucleotide analogues

A series of 5-substituted 3-phosphonylated isoxazolidines have been obtained via cycloaddition of N-methyl-C-(diethoxyphosphoryl)nitrone with N-heteroaromatic acrylamides. Good trans/cis diastereoselectivities (d.e. 58-76%) of isomeric (3-diethoxyphosphoryl)isoxazolidines were observed. cis-and trans-Isoxazolidine phosphonates were evaluated for their antiviral activity against a broad range of DNA and RNA viruses but were found inactive. Their cytostatic activity toward L1210, CEM, and HeLa cells was also established, and compounds cis-12r and trans-11r having a 2,2-difluorobenzo[d][1,3]dioxole moiety slightly inhibited proliferation of HeLa cells at IC50 values of 186 and 179 M, respectively.

Exploring DOXP-reductoisomerase binding limits using phosphonated N-aryl and N-heteroarylcarboxamides as DXR inhibitors

DOXP-reductoisomerase (DXR) is a validated target for the development of antimalarial drugs to address the increase in resistant strains of Plasmodium falciparum. Series of aryl- and heteroarylcarbamoylphosphonic acids, their diethyl esters and disodium salts have been prepared as analogues of the potent DXR inhibitor fosmidomycin. The effects of the carboxamide N-substituents and the length of the methylene linker have been explored using in silico docking studies, saturation transfer difference NMR spectroscopy and enzyme inhibition assays using both EcDXR and PfDXR. These studies indicate an optimal linker length of two methylene units and have confirmed the importance of an additional binding pocket in the PfDXR active site. Insights into the constraints of the PfDXR binding site provide additional scope for the rational design of DXR inhibitors with increased ligand-receptor interactions.

Affinity adsorption mechanism studies of adsorbents C1-Zn(II) for uremic middle molecular peptides containing Asp-Phe-Leu-Ala-Glu sequence

To exploit efficient adsorbents for removing middle molecular peptides containing DFLAE (DE5, a typical peptide sequence accumulated in uremic serum) sequence by hemoperfusion, we designed and synthesized three affinity adsorbents (C1-Zn2+, C2-Zn2+ and C3-Zn2+) that could have high affinity to DE5. Subsequently, we evaluated the corresponding adsorption ability of each adsorbent by static adsorption experiments and isothermal titration calorimetry (ITC). The results showed that C1-Zn2+ had the best adsorption ability to DE5-containing peptides and the adsorption capacity for DE5 was 8.52 mg/g. By changing the adsorption conditions, the adsorption mechanism was elucidated. The main driving force of the adsorption is metal-carboxyl coordination and the hydrophobic force affords the cooperative effect. It is expected that our present work can provide basic understanding for the design of adsorbents with high affinity and selectivity towards oligopeptides.

Synthesis of [11C]/[13C]acrylamides by palladium-mediated carbonylation

Two methods are presented for the synthesis of acrylamides labelled with 11C (β+, t1/2 = 20.4 min) and 13C in the carbonyl position. In the first method, [1- 11C]acrylic acid is synthesised from [11C]carbon monoxide by palladium-mediated hydroxycarbonylation of acetylene. The labelled carboxylic acid is converted into the acyl chloride and subsequently treated with amine to yield N-benzyl[carbonyl-11C]acrylamide. The second method utilizes [11C]carbon monoxide in a palladium-mediated carbonylative cross-coupling of vinyl halides and amines. A higher radiochemical yield is achieved with the latter method and the amount of amine needed is decreased to 1/20. The 11C-labelled acrylamides were isolated in up to 81 % decay-corrected radiochemical yield. Starting from 10 ± 0.5 GBq of [ 11C]carbon monoxide, N-benzyl[carbonyl-11C]acrylamide was obtained in 4 min with a specific radioactivity of 330 ± 4 GBq μmol-1. Co-labelling with 11C and 13C enabled confirmation of the labelled position by 13C NMR spectroscopy. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

N-(6-Methyl-2-pyridyl)acrylamide: a case of amide hydrolysis without the assistance of acid or base in the synthesis of water-driven H-bonded polymeric chains

Amide hydrolysis of N-(6-methyl-2-pyridyl)acrylamide without the assistance of either acid or base produces the aminopyridinium carboxylate salt at low or room temperature. The carboxylate ion and the free amine functionalities are cooperatively involved in hydrogen bonding with lattice water to form a new hydrogen-bonded polymeric chain.