339159-93-2

Upstream product

• 108-31-6 maleic anhydride 
• 92-67-1 4-phenylalanine 

Downstream Products

• 58609-75-9 N-(p-phenylphenyl)maleimide 

Relevant academic research and scientific papers

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 spectroscopic evidences of N-arylmaleimides and N-aryl-2,3-dimethylmaleimides

A series of N-arylmaleimides (N-aryl-MI) and N-aryl-2,3-dimethylmaleimides (N-aryl-DiMeMI) were prepared by condensation of primary amines with maleic anhydride (MAn) and 2,3-dimethylmaleic anhydride (DiMeMAn), respectively. Preparation of N-aryl-MI proceeded through the formation of N-arylmaleamic acid, which subsequently cyclized to N-aryl-MI. In the reaction of N-arylamines with DiMeMAn, cyclic condensation products were formed in one step. By means of one- and two-dimensional 1H and 13C NMR spectroscopy it was proven that N-aryl-DiMeMI and not isomaleimides were formed by a one step reaction.

Novel compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents

The present invention relates to novel compounds that can be used as antiinflammatory, immunomodulatory and antiproliferatory agents. In particular the invention refers to new compounds which inhibit dihydroorotate dehydrogenase (DHODH), a process for their manufacture, pharmaceutical compositions containing them and to their use for the treatment and prevention of diseases, in particular their use in diseases where there is an advantage in inhibiting dihydroorotate dehydrogenase (DHODH).

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.

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.