36342-10-6

Usage

Uses

Used in Pharmaceutical Synthesis:
(2E)-4-[(4-nitrophenyl)amino]-4-oxobut-2-enoic acid is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs. Its unique structure allows it to be a key component in creating molecules with specific therapeutic properties.
Used in Biochemistry Research:
In the field of biochemistry, (2E)-4-[(4-nitrophenyl)amino]-4-oxobut-2-enoic acid serves as a valuable compound for research purposes. Its distinctive features make it suitable for studying various biochemical interactions and mechanisms, potentially leading to advancements in understanding biological processes.
Used in Dye and Colorant Production:
(2E)-4-[(4-nitrophenyl)amino]-4-oxobut-2-enoic acid is utilized as a component in the production of dyes and colorants due to its vibrant yellow color and chemical composition. Its properties allow it to be a significant contributor to the coloration of various products, offering a wide range of applications across different industries.

Upstream product

• 108-31-6 maleic anhydride 
• 785-81-9 4-nitro-N-(phenylmethylene)benzenamine 
• 627-63-4 fumaryl dichloride 
• 100-01-6 4-nitro-aniline 
• 80818-24-2 (Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid 

Downstream Products

• 37904-11-3 3-chloro-1-(4-nitrophenyl)pyrrolidine-2,5-dione 
• 305373-30-2 N-(4-nitro-phenyl)-2-(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl)-acetamide 
• 80167-59-5 (E)-3-(4-Nitro-phenylcarbamoyl)-acrylic acid methyl ester 
• 4338-06-1 N-(4-nitrophenyl)maleimide 
• 59333-51-6 5-[N-(4-nitrophenyl)-imino]-5H-furan-2-one 
• 105450-98-4 Cr(COOCHCHCONHC₆H₄NO₂)3 
• 29236-11-1 2,3-dichloro-N-(p-nitrophenyl)maleimide 

Relevant academic research and scientific papers

Thermally Sensitive Protecting Groups for Cysteine, and Manufacture and Use Thereof

In a preferred embodiment, there is provided a protecting group for protecting the thiol side chain of a cysteine residue, the protecting group comprising a Diels-Alder cycloadduct of a furan and a maleimide, and optionally, a linker interposed between the thiol side chain and the Diels-Alder cycloadduct.

Synthesis, characterization crystal structures and DNA binding studies of zinc complexes with oxygen and nitrogen donor ligands

Three zinc metal complexes viz, [Zn(L1)2phen] (1), [Zn2(L2)4(bipy)2] (2) and [Zn(L2)2bipy·H2O] (3) where HL1 = 4-(o-toluidino)-4-oxobutanoic acid

Design, synthesis and biological evaluation of novel 3,4-dihydro-2(1H)-quinolinone derivatives as potential chitin synthase inhibitors and antifungal agents

A series of 3,4-dihydro-2(1H)-quinolinone derivatives contained butenediamide fragment were designed and synthesized. Their inhibition potency against chitin synthase and antimicrobial activities were screened in vitro. The enzymatic assays showed that all the synthesized compounds had inhibition potency against chitin synthase at concentration of 300 μg/mL. Compound 2d displayed excellent potency with inhibition percentage (IP) value of 82.3%, while IP value of the control polyoxin B was 87.5%. Compounds 2b, 2e and 2s whose IP values were above 70% showed good inhibition potency against chitin synthase. Moreover, the IC50 value of 2b was comparable with that of polyoxin B (0.09 mM). The Ki of compound 2b was 0.12 mM and the result from Lineweaver-Burk plot showed that 2b was non-competitive inhibitor to bind chitin synthase. The antifungal experiment showed that these compounds had excellent antifungal activity against fungal strains, especially for candida albicans. The antifungal activities against C .albicans of compounds 2b, 2d, 2e and 2l were comparable with that of fluconazole and were superior to that of polyoxin B. Meanwhile, the other compounds against C. albicans showed better antifungal activity (MIC 2 μg/mL) than polyoxin B except for compound 2n (MIC 4 μg/mL). The trial of drug combination use showed that these synthesized compounds had synergistic effects with fluconazole and polyoxin B. It indicated that these compounds were not competing with polyoxin B to bind with chitin synthase, which was also consistence with the result of enzymatic assays. The antibacterial experiment showed that these compounds had no activity against selected strains including three Gram-positive and three Gram-negative bacteria. These results showed that the designed compounds were chitin synthase inhibitors and had selective antifungal activity.

Novel p-nitrophenyl maleanilic acid and its organometallic chelates of Cr, Mo and W carbonyls structure evaluation using different techniques and chromium chelate cytotoxicity

Novel p-nitrophenyl maleanilic acid bidentate free ligand (PNMA) was synthesized eco-friendly by solvent free reaction between 4-nitroaniline and maleic anhydride. Some novel mixed ligand organometallic chelates of formulae [M(CO)4L] (M = Cr, Mo, or W and

Synthesis of Tetrahydroisoindolinones via a Metal-Free Dehydrogenative Diels-Alder Reaction

A metal-free dehydrogenative Diels-Alder reaction of substituted alkenes for the synthesis of tetrahydroisoindolinones has been exploited for the first time. This new method features functional group tolerance and broad substrate scope, providing an efficient access to biologically active tetrahydroisoindolinone skeletons with endo steroselectivity in good to excellent yields. (Figure presented.).

Alizarin red S-TiO2-catalyzed cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation

A very low amount of organic dye (Alizarin red S) sensitized TiO2 and it was successfully used to catalyze cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions under visible light irradiation. The modified TiO2 photocatalyst efficiently, for the first time, advanced [4+2] cyclization of N,N-dimethylanilines and maleimides to the corresponding tetrahydroquinolines in air atmosphere. The reaction proceeds through α-amino radicals without additional oxidant at ambient temperature to afford products in good to excellent yields.

Solvent-free and room temperature visible light-induced C-H activation: CdS as a highly efficient photo-induced reusable nano-catalyst for the C-H functionalization cyclization of: T -amines and C-C double and triple bonds

Nano-sized CdS was successfully prepared, fully characterized and applied as a highly efficient reusable photocatalyst for the synthesis of pyrrolo[3,4-c]quinolone and pyrrolo[2,1-a]isoquinoline-8-carboxylate derivatives through a condensation reaction of N,N-dimethylanilines or alkyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetates with maleimides via a C-H activation approach under benign and eco-friendly conditions at room temperature without using any solvent and oxidant under visible light irradiation. Besides, the prepared photocatalyst has been successfully applied for the condensation reaction of N,N-dimethylanilines with alkyl but-2-ynedioates or phenyl acetylenes for the synthesis of novel 1,2-dihydroquinoline-3,4-dicarboxylate and aryl-1,2-dihydroquinoline derivatives for the first time. Using this method, all favourable products were obtained in good yields and relatively short reaction times under benign conditions with the application of visible light irradiation, a renewable energy source. The catalyst was easily recovered and reused several times without any loss of its activity.

Acetylcholinesterase inhibition by products generated in situ from the transformation of N-arylisomaleimides

When N-arylisomaleimides were transformed under enzymatic reaction conditions, the transformation reaction proved to be influenced by electronic effects. This was demonstrated qualitatively by 1H NMR spectroscopy and quantitatively by monitoring the kinetic of isomerization of N-phenylisomaleimide to N-phenylmaleimide. Subsequently, the first pseudo-order and activation energy (Ea) of the process were determined. The compounds showed in situ influence on AChE inhibition. The derivatives with electron-withdrawing groups exhibited a better effect than those having electron-donating groups. The in silico experiments show that the ligands evaluated established interactions with the CAS site. This suggests that these compounds could be useful for generating better reversible and competitive inhibitors of AChE.

Graphene Oxide as a Carbocatalyst for a Diels–Alder Reaction in an Aqueous Medium

The Diels–Alder (DA) reaction, a [4+2] cycloaddition reaction, is highly important in synthetic organic chemistry and is frequently used in the synthesis of natural products containing six-membered rings. Herein, we report an efficient protocol for the DA reaction between 9-hydroxymethylanthracene and N-substituted maleimides using two-dimensional graphene oxide (GO) as a heterogeneous carbocatalyst in an aqueous medium at room temperature. High yields, a wide substrate scope, low temperature, excellent functional group tolerance, atom economy, and water as a green solvent are noteworthy features of this protocol. The heterogeneous GO catalyst can be easily recovered and used multiple times without any significant loss in catalytic activity.

Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita

Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 ± 1.3, 5.1 ± 3.4, 16.2 ± 5.4, and 19.0 ± 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 ± 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at 50 mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.