- A rapid and simple amine-catalyzed microwave-assisted isomerization of maleamides into fumaramides
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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.
- Majce, Vita,Ko?evar, Marijan,Polanc, Slovenko
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supporting information; experimental part
p. 3287 - 3290
(2011/06/28)
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- Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors
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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.
- Matuszak, Nicolas,Muccioli, Giulio G.,Labar, Geoffray,Lambert, Didier M.
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experimental part
p. 7410 - 7420
(2010/04/30)
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- Substituent chemical shifts of N-arylsuccinanilic acids, N-arylsuccinimides, N-arylmaleanilic acids, and N-arylmaleimides
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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.
- Lee, Hye Sun,Yu, Ji Sook,Lee, Chang Kiu
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scheme or table
p. 711 - 715
(2010/07/05)
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- Synthesis and antifungal activity of N-(alkyl/aryl)-2-(3-oxo-1,4- benzothiazin-2-yl)acetamide
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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.
- Gupta,Wagh
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p. 697 - 702
(2007/10/03)
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- INFLUENCE OF MEDIUM AND SUBSTITUENTS ON ACYLATION OF AROMATIC AMINES AND THEIR POLYMERIC ANALOGS WITH MALEIC ANHYDRIDE
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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.
- Donya, A. P.,Pakter, M. K.,Sokhina, S. I.
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p. 2093 - 2097
(2007/10/02)
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- Esterification of Maleanilic Acids: Intramolecular Esterification Through Imidate Ester
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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.
- Kumar, Baldev,Verma, Raman K.,Singh, Harjit
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p. 692 - 696
(2007/10/02)
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