17392-68-6

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-METHOXY-PHENYL)-PYRROLE-2,5-DIONE is used as a key intermediate for the synthesis of various pharmaceuticals, leveraging its reactivity and structural features to contribute to the development of new drugs.
Used in Agrochemical Industry:
Similarly, in the agrochemical sector, 1-(2-METHOXY-PHENYL)-PYRROLE-2,5-DIONE serves as a building block for the creation of agrochemicals, potentially enhancing crop protection and yield.
Used in Medicinal Chemistry Research:
1-(2-METHOXY-PHENYL)-PYRROLE-2,5-DIONE is utilized as a subject of study in medicinal chemistry for its potential biological activities, particularly in exploring its anticancer and anti-inflammatory properties, which could lead to advancements in treatment options.
Used in Synthetic Chemistry:
As a valuable intermediate, 1-(2-METHOXY-PHENYL)-PYRROLE-2,5-DIONE is instrumental in the preparation of diverse heterocyclic compounds, expanding the scope of synthetic chemistry and contributing to the discovery of novel chemical entities.

InChI:InChI=1/C11H9NO3/c1-15-9-5-3-2-4-8(9)12-10(13)6-7-11(12)14/h2-7H,1H3

Upstream product

• 31460-26-1 (2-methoxyphenyl)maleamic acid 
• 90-04-0 2-methoxy-phenylamine 
• 110-16-7 maleic acid 
• 36847-94-6 C₁₁H₁₁NO₄ 
• 108-31-6 maleic anhydride 
• 67-56-1 methanol 

Downstream Products

• 89143-25-9 1-(2-Methoxy-phenyl)-3-piperidin-1-yl-pyrrolidine-2,5-dione 
• 106058-50-8 1-(2-Methoxy-phenyl)-3-(4-phenylsulfanyl-phenylamino)-pyrrolidine-2,5-dione 
• 106058-30-4 1-(2-Methoxy-phenyl)-3-(4-methoxy-phenylamino)-pyrrolidine-2,5-dione 
• 106058-40-6 3-(4-Ethoxy-phenylamino)-1-(2-methoxy-phenyl)-pyrrolidine-2,5-dione 
• 152903-99-6 3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-4-methoxy-benzenesulfonyl chloride 
• 1047646-60-5 9-hydroxy-2-(2-methoxy-phenyl)-9,9a-dihydro-3aH-4-thia-2-aza-cyclopenta[b]naphthalene-1,3-dione 
• 810629-29-9 C₁₇H₁₈N₄O₅ 
• 1352413-55-8 N-(2-methoxyphenyl)-1,3-dimethyl-2,4,7-trioxo-1,2,3,4,5,6,7,8-octahydropyrido[2,3-d]pyrimidine-5-carboxamide 
• 1282121-02-1 N-(2-methoxyphenyl)-2,4,7-trioxo-1-(2-phenylethyl)-1,2,3,4,5,6,7,8-octahydropyrido[2,3-d]pyrimidine-5-carboxamide 

Relevant academic research and scientific papers

The CH-π interactions of methyl ethers as a model for carbohydrate-N-heteroarene interactions

CH-π interactions have been cited as an important contributor to carbohydrate recognition. To determine whether N-heterocycles form stronger CH-π interactions, the interactions of methyl ether groups with heterocyclic and nonheterocyclic aromatic surfaces

1,3-dipolar cycloaddition: Free catalytic synthesis and esophageal cancer activity of new 1,2,3-triazole-oxydianiline-maleimide hybrids

A new series of 1,2,3-triazole-oxydianiline-maleimide hybrids 12-15 was synthesized by using 1,3-dipolar cycloaddition reaction of N-Arylmaleimides 6-9 with 4,4'-oxybis(azidobenzene) 11 under an efficient and free catalytic reaction. All the newly synthesized hybrids were characterized by their 1H NMR, F-TIR, Mass spectral data and melting points. The cytotoxic activities (in vitro) of selected hybrids against esophageal cancer of human cell line (SKG) were evaluated by MTT assay. Among them, hybrid 13 exhibited a potent inhibition activity with the IC50 value of 1.61±0.01 μM against esophageal cancer cell (SKG). Cellular mechanism investigations in esophageal carcinoma cells (SKG) elucidated that hybrid 13 inhibited cell growths in vitro and arrested cell cycle at an environmental phase. These results revealed that hybrid 13 holds a promising anticancer agent with the enhancement of further clinical applications in drug discovery field.

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.

Photoorganocatalysed and visible light photoredox catalysed trifluoromethylation of olefins and (hetero)aromatics in batch and continuous flow

Trifluoromethylation of olefins and (hetero)aromatics with sodium triflinate as CF3 source and readily accessible benzophenone derivatives as photosensitisers has been developed in batch and flow. The use of an iridium-based photocatalyst enables the trifluoromethylation to proceed under visible light irradiation.

Discovery and structural optimization of pyrazole derivatives as novel inhibitors of Cdc25B

Structural optimization and preliminary structure-activity relationship studies of a series of N-substituted maleimide fused-pyrazole analogues with Cdc25B inhibitory activity, starting from a high-throughput screening hit, are illustrated. A simplified 3,5-diacyl pyrazole analogue was obtained as the most potent compound (118, IC50 = 0.12 μM) with a 270-fold increase in potency.

Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors

The endocannabinoid 2-arachidonoylglycerol (2-AG) plays a major role in many physiological processes, and its action is quickly terminated via enzymatic hydrolysis catalyzed by monoglyceride lipase (MGL). Regulating its endogenous level could offer therapeutic opportunities; however, few selective MGL inhibitors have been described so far. Here, we describe the synthesis of N-substituted maleimides and their pharmacological evaluation on the recombinant human fatty acid amide hydrolase (FAAH) and on the purified human MGL. A few N-arylmaleimides were previously described (Saario, S. M.; Salo, O. M.; Nevalainen, T.; Poso, A.; Laitinen, J. T.; Jarvinen, T.; Niemi, R. Characterization of the Sulfhydryl-Sensitive Site in the Enzyme Responsible for Hydrolysis of 2-Arachidonoylglycerol in Rat Cerebellar Membranes. Chem. Biol. 2005, 12, 649-656) as MGL inhibitors, and along these lines, we present a new set of maleimide derivatives that showed low micromolar IC50 and high selectivity toward MGL vs FAAH. Then, structure-activity relationships have been investigated and, for instance, 1-biphenyl-4-ylmethylmaleimide inhibits MGL with an IC50 value of 790 nM. Furthermore, rapid dilution experiments reveal that these compounds act as irreversible inhibitors. In conclusion, N-substituted maleimides constitute a promising class of potent and selective MGL inhibitors.

Synthesis and antimicrobial activities of N-substituted imides

In the field of our research programs concerning novel antimicrobial agents, a series of N-substituted imides was synthesized. These compounds were obtained by cyclization of amido-acids in acetic anhydride/sodium acetate or hexamethyldisilazane/zinc bromide for the hydroxy-aromatic derivatives. The hydroxy-alkyl maleimides were directly prepared by condensation of the corresponding amino-alcohol with maleic anhydride in boiling toluene. Most of N-substituted maleimides showed an interesting antimicrobial activity towards bacteria from the ATCC collection (Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) but the MIC values for P. aeruginosa were always high (128 μg/ml). The imides with alkyl substituents showed higher activities than aromatic analogues with MIC values in the range of 8-32 μg/ml. Comparatively, succinimides were practically inactive.

1H and 13C NMR spectra for a series of arylmaleamic acids, arylmaleimides, arylsuccinamic acids and arylsuccinimides

The 1H and 13C NMR spectra of 17 succinic anhydride derivatives and 25 maleic anhydride derivatives were completely assigned using one- and two-dimensional NMR techniques. Copyright

CHLOROSULFONATION OF N-ARYLMALEIMIDES

N-Phenylmaleimides, o-, m- and p-substituted (1) react with excess chlorosulfonic acid to give the corresponding sulphonyl chlorides (2-5).These were condensed with amines and phenols to give derivatives (7-29) which underwent hydrolysis or ammonolysis to give respectively the sulfamoyl maleamic acids (31-34) and sulfamoyl maleamides (35-39). Key words: N-arylmaleimides; chlorosulfonation

Chlorosulfonation of N-arylmaleimides

N-phenylmaleimides, o-, m- and p-substituted (1) reacted with excess chlorosulfonic acid to give the corresponding sulphonyl chlorides (2-5). These were condensed with amines and phenols to give derivatives (7-29) which underwent hydrolysis or ammonolysis