42537-50-8

Usage

Uses

Used in Pharmaceutical Research:
(2Z)-4-[(3-methylphenyl)amino]-4-oxobut-2-enoic acid is used as a building block in the synthesis of various pharmaceutical and biologically active compounds due to its unique structure and the presence of the amino group. This makes it a promising candidate for the development of new drugs with potential medicinal applications.
Used in Organic Synthesis:
In the field of organic synthesis, (2Z)-4-[(3-methylphenyl)amino]-4-oxobut-2-enoic acid serves as an important intermediate for creating a range of chemical products. Its versatility in chemical reactions allows for the production of diverse compounds with various applications across different industries.

Upstream product

• 108-31-6 maleic anhydride 
• 108-44-1 1-amino-3-methylbenzene 

Downstream Products

• 107125-42-8 (Z)-4-Ethoxy-4-[(E)-m-tolylimino]-but-2-enoic acid methyl ester 
• 107114-47-6 3-chloro-1-m-tolyl-pyrrolidine-2,5-dione 
• 107125-39-3 (Z)-3-m-Tolylcarbamoyl-acrylic acid isopropyl ester 
• 500551-65-5 3-m-tolylcarbamoyl-acrylic acid methyl ester 
• 1313395-68-4 N⁽¹⁾-benzyl-N⁽⁴⁾-(m-tolyl)fumaramide 
• 1313395-58-2 N⁽¹⁾-benzyl-N⁽⁴⁾-(m-tolyl)maleamide 
• 96824-22-5 (Z)-3-m-Tolylcarbamoyl-acrylic acid ethyl ester 
• 134616-46-9 2-(3-Oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl)-N-m-tolyl-acetamide 
• 915711-58-9 3-m-tolylcarbamoyl-acrylic acid methyl ester 
• 20299-79-0 1-(3-methylphenyl)-1H-pyrrole-2,5-dione 
• 107125-41-7 (Z)-4-Ethoxy-4-[(E)-m-tolylimino]-but-2-enoic acid 
• 54012-35-0 2-(3-anilino-4-oxo-2-thioxo-thiazolidin-5-yl)-N-m-tolyl-acetamide 

Relevant academic research and scientific papers

Nanoporous hypercrosslinked polymers containing Tg enhancing comonomers

Hypercrosslinked polymers containing functionalized alternating copolymer sequences of substituted stilbene or styrene and N-aryl substituted maleimides have been synthesized. Alternating copolymers containing these comonomers possess semi-rigid structures, and incorporation of these units into the precursor polymer particles for hypercrosslinking leads to a systematic increase in Tg and chain stiffness of these materials as the concentration of the comonomers is increased. Surface area and porosity of the subsequent hypercrosslinked polymers were investigated using nitrogen adsorption/desorption isotherms at 77 K. These hypercrosslinked polymers exhibit BET surface areas ranging from 1058 m2/g at 25 mol% alternating copolymer incorporation down to loss of measurable surface area at ca. 60% incorporation. The experimental surface area results correlate with predictions from simulations and serve as model systems for future studies on specifically functionalized hypercrosslinked polymer particles.

A rapid and simple amine-catalyzed microwave-assisted isomerization of maleamides into fumaramides

An improved, efficient, and simple method for the synthesis of nonsymmetrical diamides of fumaric acid is reported. Starting from commercially available substrates, maleic diamides are formed in two steps, and then isomerized in a focused microwave reactor in acetonitrile as the solvent in the presence of a catalytic amount of piperidine, giving the corresponding fumaramides in high yields and purity.

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.

Substituent chemical shifts of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides

NMR spectra of a series of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides were examined to estimate the electronic effect of the amide and imide groups on the chemical shifts of the hydrogen and carbon nuclei of the benzene ring.

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.

Non-hydroxylic clathrate hosts of [4 + 2]π cycloadducts of phencyclone and N-arylmaleimides: Recognition of aromatic guests

A series of non-hydroxylic crystalline host compounds, [4 + 2]π cycloadducts of phencyclone and N-arylmaleimides having a bicyclo[2.2.1]heptene-7-one system, was synthesized and their inclusion behavior investigated. X-Ray crystal analyses of the inclusion compounds of the N-(1-naphthyl) derivative with butan-2-one, the N-(m-tolyl) derivative with p-xylene, together with the guest-free host and the N-(p-tolyl) derivative with m-xylene indicate that the "space" surrounded by the phenanthrene ring, two phenyl rings and bridge carbonyl of the 1,3-diphenyl-1,3-dihydrocyclopenta[l]phenanthren-2-one moiety plays an important role, not only in the formation of inclusion complexes with the aromatic guests but also in host-host interactions. In every case, the N-aryl succinimide assists complex formation with the guests, in which the weak lattice forces due to C-H ... π and C-H ... O interactions are operative. Methyl-substituted benzenes are effectively recognized by the C-H ... π interactions between the guest molecules and the phenanthrene ring of the hosts.

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.

INFLUENCE OF MEDIUM AND SUBSTITUENTS ON ACYLATION OF AROMATIC AMINES AND THEIR POLYMERIC ANALOGS WITH MALEIC ANHYDRIDE

Correlation relationships describing the influence of substituents and solvents on the rate of acylation of aromatic amines and their polymeric analogs with maleic anhydride have been derived.

Esterification of Maleanilic Acids: Intramolecular Esterification Through Imidate Ester

Maleanilic acids are easily esterified at room temperature with an abs. alcohol in the presence of thionyl chloride.It has been shown to proceed through an intramolecular migration of alkyl group of the intermediate imidate ester.