36847-94-6

Usage

Uses

Used in Coordination Polymer Synthesis:
N-(2-Methoxyphenyl)maleamic acid is used as a building block for the synthesis of coordination polymers due to its ability to form metal complexes. This application is valuable in creating new materials with specific properties for various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical field, N-(2-Methoxyphenyl)maleamic acid is used as a precursor or intermediate in the development of new drugs. Its unique chemical properties make it a promising candidate for the synthesis of pharmaceutical compounds with potential therapeutic applications.
Used in Materials Science:
N-(2-Methoxyphenyl)maleamic acid is utilized in materials science for the development of new materials with specific characteristics. Its ability to form metal complexes allows for the creation of materials with tailored properties for various applications.
Used as a Ligand in Catalyst Development:
N-(2-Methoxyphenyl)maleamic acid is used as a ligand in the development of new catalysts. Its unique properties enable the design of catalysts with improved performance and selectivity in various chemical reactions.
Used in Metal Purification:
N-(2-Methoxyphenyl)maleamic acid is employed in the purification of metals, where it acts as a chelating agent to selectively bind and separate metal ions. This application is crucial in the production of high-purity metals for various industries.

InChI:InChI=1/C11H11NO4/c1-16-9-5-3-2-4-8(9)12-10(13)6-7-11(14)15/h2-7H,1H3,(H,12,13)(H,14,15)/p-1/b7-6+

Upstream product

• 108-31-6 maleic anhydride 
• 90-04-0 2-methoxy-phenylamine 

Downstream Products

• 17392-68-6 1-(2-methoxyphenyl)maleimide 
• 59652-98-1 6β-[3-(2-methoxy-phenylcarbamoyl)-acryloylamino]-penicillanic acid 

Relevant academic research and scientific papers

Synthesis, physicochemical characterization, DNA binding and in silico studies of (E)-4-((2-methoxyphenyl)amino)-4-oxobut-2-enoic acid and its triorganotin complexes

The ligand, (E)-4-((2-methoxyphenyl)amino)-4-oxobut-2-enoic acid, and its tri-butylstannyl (E)-4-((2-methoxyphenyl)amino)-4-oxobut-2-enoate, trimethylstannyl (E)-4-((2-methoxyphenyl)amino)-4-oxobut-2-enoate and triethylstannyl (E)-4-((2-methoxyphenyl)amino)-4-oxobut-2-enoate complexes were obtained and characterized by different techniques. The spectroscopic data revealed the presence of the OH in the FTIR and NMR spectra of the (E)-4-((2-methoxyphenyl)amino)-4-oxobut-2-enoic acid and the absence of this peak in the spectra of the complexes confirm their successful formation. The geometry confirmation was done using single-crystal X-ray diffraction and found a 5-coordinated distorted trigonal bipyramidal comprising of the O1 of the carboxylate moiety, O3 of the amide moiety occupying the axial position while the three equatorial positions were occupied by the carbon atoms of the three butyl groups. The result of the DNA interaction of the representative compounds explored an intercalative binding mode as confirmed by UV-Visible spectroscopy and viscometry. The in silico study performed by SwissADME webserver suggested that reported compounds obey the rules of drug-likeness. Graphical abstract: [Figure not available: see fulltext.]

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.

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.

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.

Curcumin-inspired cytotoxic 3,5-bis(arylmethylene)-1-(N-(ortho-substituted aryl)maleamoyl)-4-piperidones: A novel group of topoisomerase II alpha inhibitors

Three series of novel 3,5-bis(arylmethylene)-1-(N-(ortho-substituted aryl)maleamoyl)-4-piperidones, designed as simplified analogs of curcumin with maleic diamide tether, were synthesized and bioevaluated. These compounds displayed potent cytotoxicity tow

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 antifungal activity of N-(alkyl/aryl)-2-(3-oxo-1,4- benzothiazin-2-yl)acetamide

A series of N-(alkyl/aryl)-2-(3-oxo-1,4-benzothiazin-2-yl)acetamide have been synthesized by condensation of substituted amines with maleic anhydride (MA) followed by cyclization with o-aminothiophenol (o-ATP). All the compounds have been screened for their antifungal activity against Tricophyton rubrum, Epidermophyton floccosum and Malassazia furfur. In the primary screening, some of the compounds exhibited appreciable activity. The structures of the synthesized compounds 7a-z have been established on the basis of elemental analysis and spectral data.

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

Reactions of cyclic anhydrides with aromatic primary amines: Part 3 - Synthesis of novel 3-(N-arylcarbamoyl)- and 3-(N-naphthylcarbamoyl)carboxylic acids

Some hitherto unreported 3-(N-arylcarbamoyl)propenoic acids 7a-h and 3-(N-naphthylcarbamoyl)propenoic acid 9 have been synthesized in excellent yields, together with some propanoic acid analogues 11a-h and 12 as potential pesticides. Structural assignments of the products are based on elemental analyses and spectral (IR, 1H NMR, mass) data.