4338-06-1

Usage

Uses

Used in Biochemical Research:
N-(4-Nitrophenyl)maleimide is used as a thiol-reactive compound for studying protein structure and function. Its reactivity with thiol groups allows researchers to modify and label proteins, providing insights into their behavior and interactions within biological systems.
Used in Protein Modification and Labeling Experiments:
N-(4-Nitrophenyl)maleimide is used as a protein-modifying agent to form stable adducts with thiol-containing proteins. This enables the investigation of protein properties, such as folding, stability, and interactions with other biomolecules.
Used in the Development of Fluorescent Probes:
N-(4-Nitrophenyl)maleimide is utilized in the creation of fluorescent probes that can be used to track and visualize the behavior of thiol-containing proteins in living cells and tissues, providing valuable information about their localization and dynamics.
Used in the Development of Biologically Active Molecules:
Due to its reactivity and versatility, N-(4-Nitrophenyl)maleimide is employed in the synthesis of biologically active molecules with potential applications in drug discovery and therapeutic development.

Upstream product

• 36342-10-6 4-(4-nitrophenylamino)-4-oxobut-2-enoic acid 
• 941-69-5 N-phenyl-maleimide 
• 30186-41-5 1-(4-nitrophenyl)pyrrole-2-carbaldehyde 
• 100-01-6 4-nitro-aniline 
• 110-16-7 maleic acid 
• 37904-11-3 3-chloro-1-(4-nitrophenyl)pyrrolidine-2,5-dione 
• 80818-24-2 (Z)-(2-methyl-4-(4-nitrophenylamino)-4-oxo)but-2-enoic acid 
• 36342-10-6 (Z)-3-(4-nitro-phenylcarbamoyl)-acrylic acid 
• 108-31-6 maleic anhydride 

Downstream Products

• 60437-33-4 2-(2-amino-4-methyl-7-oxo-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-6-yl)-N-(4-nitro-phenyl)-acetamide 
• 70464-55-0 3ξ-(4-methoxy-phenyl)-5-(4-nitro-phenyl)-2-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 35216-34-3 2-(4-chloro-phenyl)-5-(4-nitro-phenyl)-3c-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 57703-45-4 2-(4-nitro-phenyl)-4,9-diphenyl-3a,4,9,9a-tetrahydro-4,9-epioxido-benzo[f]isoindole-1,3-dione 
• 35216-29-6 2-(4-tert-butyl-phenyl)-5-(4-nitro-phenyl)-3t-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 35216-29-6 2-(4-tert-butyl-phenyl)-5-(4-nitro-phenyl)-3c-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 57703-50-1 6,7-dimethyl-2-(4-nitro-phenyl)-4,9-di-p-tolyl-3a,4,9,9a-tetrahydro-4,9-epioxido-benzo[f]isoindole-1,3-dione 
• 70464-63-0 5-(4-nitro-phenyl)-3-(2,4,6-trimethyl-phenyl)-(3ar,6ac)-3a,6a-dihydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 35216-15-0 5-(4-nitro-phenyl)-2,3t-diphenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 35216-15-0 5-(4-nitro-phenyl)-2,3c-diphenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 70518-37-5 5-(4-nitro-phenyl)-2,3ξ-diphenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 70464-58-3 3ξ-(4-bromo-phenyl)-5-(4-nitro-phenyl)-2-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 70464-56-1 3ξ,5-bis-(4-nitro-phenyl)-2-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 70464-57-2 3ξ-(4-dimethylamino-phenyl)-5-(4-nitro-phenyl)-2-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 

Relevant academic research and scientific papers

Dipolar cycloadditions of imidazoline 3-oxides with N-arylmaleimides. Synthesis and diethylamine induced ring-opening of exo and endo hexahydro-7-oxa-2,5,6a-triaza-cyclopenta[a]pentalene-1,3-diones

1,4-Diarylimidazoline 3-oxides react with N-arylmaleimides in benzene to give predominantly the corresponding endo adducts. Chiral imidazoline 3-oxides react diastereospecifically (cis configuration of the tetrahydroimidazo ring) and diastereoselectively to give cis-endo adducts. The effects of substituents on the aromatic ring of the maleimide was investigated. The presence of electron-withdrawing or releasing groups have minor effect on the total yields but more pronounced is the effect on the ratio of exo and endo diastereomers. The adducts undergo an interesting and unprecedented ring-opening in the presence of secondary amines to give deoxygenated 3-imidazoline 3-oxides instead of the expected double cis elimination products. Tertiary amines did not induce any reaction.

Oxidation of 1-(4-nitrophenyl)-2-formylpyrrole

Pyrrole aldehydes interact with oxidizing agents to yield products which are oxidized to different degrees. Pyrrolecarboxylic acids are formed under the influence of silver oxides, an alkaline solution of permanganate, and 2-10% sulfuric acid [1-3]. With

Exploiting: Exo and endo furan-maleimide Diels-Alder linkages for the functionalization of organoruthenium complexes

Diels-Alder cycloadditions involving furans and maleimides are extensively used in organic chemistry and materials synthesis. Given the promising advances of organoruthenium complexes in therapy, we explored the possibility of exploiting such Diels-Alder linkages as a mean to modulate their biological properties. This journal is

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.

Dual organic dyes as a pseudo-redox mediation system to promotion of tandem oxidation /[3+2] cycloaddition reactions under visible light

An atom- and step-economy protocol has been developed to synthesize some new biologically active pyrrolo[2,1-a]isoquinoline alkaloids via redox mediation system under visible light irradiation. A vast variety of double and triple bonds, as dipolarophiles, treated with in situ generated azomethine ylides to prepare corresponding products in good to excellent yields. This metal-free method effectively promoted oxidation/[3 + 2] cycloaddition/oxidative/aromatization domino reaction without further oxidant using dual organic dyes as pseudo-redox mediation system. Besides, for most of the products, product precipitate was readily separated from reaction media. To the best of our knowledge, this is the first report of dual dyes as a pseudo-redox mediation system.

Functional Porphyrinic Metal–Organic Framework as a New Class of Heterogeneous Halogen-Bond-Donor Catalyst

Biomimetic metal-organic frameworks have attracted great attention as they can be used as bio-inspired models, allowing us to gain important insights into how large biological molecules function as catalysts. In this work, we report the synthesis and utilization of such a metal-metalloporphyrin framework (MMPF) that is constructed from a custom-designed ligand as an efficient halogen bond donor catalyst for Diels–Alder reactions under ambient conditions. The implementation of fabricated halogen bonding capsule as binding pocket with high-density C?Br bonds enabled the use of halogen bonding to facilitate organic transformations in their three-dimensional cavities. Through combined experimental and computational studies, we showed that the substrate molecules diffuse through the pores of the MMPF, establishing a host-guest system via the C?Br???π interaction. The formation of halogen bonds is a plausible explanation for the observed boosted catalytic efficiency in Diels–Alder reactions. Moreover, the unique capability of MMPF highlights new opportunities in using artificial non-covalent binding pockets as highly tunable and selective catalytic materials.

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.).

Preparation and Characterization of a Small Library of Thermally-Labile End-Caps for Variable-Temperature Triggering of Self-Immolative Polymers

The reaction between furans and maleimides has increasingly become a method of interest as its reversibility makes it a useful tool for applications ranging from self-healing materials, to self-immolative polymers, to hydrogels for cell culture and for the preparation of bone repair. However, most of these applications have relied on simple monosubstituted furans and simple maleimides and have not extensively evaluated the potential thermal variability inherent in the process that is achievable through simple substrate modification. A small library of cycloadducts suitable for the above applications was prepared, and the temperature dependence of the retro-Diels-Alder processes was determined through in situ 1H NMR analyses complemented by computational calculations. The practical range of the reported systems ranges from 40 to >110 °C. The cycloreversion reactions are more complex than would be expected based on simple trends expected based on frontier molecular orbital analyses of the materials.

Cp?Co(III)-Catalyzed C-H Alkylation with Maleimides Using Weakly Coordinating Carbonyl Directing Groups

A novel protocol for ortho-C-H alkylation of aromatic and heteroaromatic ketones and esters under Cp?Co(III) catalysis has been developed for the first time. The reaction proceeds through initial cyclometalation via weak chelation-assisted C-H bond activation, followed by coordination of activated alkene, insertion between Co-C, and protodemetalation.

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.