31460-26-1

Usage

Uses

Used in Pharmaceutical Industry:
Acemetacin is utilized as an analgesic and anti-inflammatory agent for the treatment of conditions such as osteoarthritis, rheumatoid arthritis, and other musculoskeletal disorders. Its efficacy in managing acute pain and inflammation has led to its common prescription for short-term use. However, it is advised to exercise caution with long-term use due to the potential for gastrointestinal side effects, including stomach ulcers and bleeding, particularly in patients with a history of such issues.
Used in Clinical Applications:
In clinical settings, Acemetacin serves as a valuable asset for the temporary relief of pain and inflammation associated with various conditions. Its role is crucial in nonsteroidal anti-inflammatory therapy, offering an alternative to steroidal options for patients who may not tolerate or are contraindicated for steroid use.

Upstream product

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

Downstream Products

• 54012-36-1 2-(3-anilino-4-oxo-2-thioxo-thiazolidin-5-yl)-N-(2-methoxy-phenyl)-acetamide 
• 17392-68-6 1-(2-methoxyphenyl)maleimide 
• 152903-99-6 3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-4-methoxy-benzenesulfonyl chloride 
• 152904-05-7 3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-N,N-diethyl-4-methoxy-benzenesulfonamide 
• 89143-25-9 1-(2-Methoxy-phenyl)-3-piperidin-1-yl-pyrrolidine-2,5-dione 
• 89143-13-5 1'-(2-Methoxy-phenyl)-[1,3']bipyrrolidinyl-2',5'-dione 
• 106058-50-8 1-(2-Methoxy-phenyl)-3-(4-phenylsulfanyl-phenylamino)-pyrrolidine-2,5-dione 
• 106058-40-6 3-(4-Ethoxy-phenylamino)-1-(2-methoxy-phenyl)-pyrrolidine-2,5-dione 
• 106058-30-4 1-(2-Methoxy-phenyl)-3-(4-methoxy-phenylamino)-pyrrolidine-2,5-dione 
• 86396-52-3 (E)-3-(2-Methoxy-phenylcarbamoyl)-acrylic acid methyl ester 
• 915711-50-1 (Z)-3-(2-Methoxy-phenylcarbamoyl)-acrylic acid methyl ester 

Relevant academic research and scientific papers

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.

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.

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

Synthesis of N-Aryl/heteroaryl/-substituted-methyl-&α-(p-substituted anilino)succinimides as Antituberculosis Agents

A series of N-Aryl/heteroaryl/substituted-methyl-α-(p-substituted anilino)succinimides (II) have been prepared and screened in vitro against H37Rv strain of Mycobacterium tuberculosis.Some of these compounds exhibit activity upto 0.39 μg/ml concentration.