36847-92-4Relevant academic research and scientific papers
The synthesis of (Z)-4-oxo-4-(arylamino)but-2-enoic acids derivatives and determination of their inhibition properties against human carbonic anhydrase I and II isoenzymes
Oktay, Koray,K?se, Leyla Polat,?endil, K?v?lc?m,Gültekin, Mehmet Serdar,Gül?in, ?lhami,Supuran, Claudiu T.
, p. 939 - 945 (2016)
The synthesis of (Z)-4-oxo-4-(arylamino)but-2-enoic acid (4) derivatives containing structural characteristics that can be used for the synthesis of several active molecules, is presented. Some of the butenoic acid derivatives (4a, 4c, 4e, 4i, 4j, 4k) are
Synthesis of Diels-Alder adducts of N-arylmaleimides by a multicomponent reaction between maleic anhydride, dienes, and anilines
Guevara-Salazar, J. Alberto,Quintana-Zavala, Delia,Jimenez-Vazquez, Hugo A.,Trujillo-Ferrara, Jose
experimental part, p. 827 - 836 (2012/07/27)
We have carried out the synthesis and characterization of some hexahydroisoindolyl benzoic acids and their corresponding ethyl esters by a multicomponent reaction (MCR) between aminobenzoic acids or aminobenzoates, maleic anhydride, and isoprene in the ab
PHTHALANILATE COMPOUNDS AND METHODS OF USE
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Page/Page column 45, (2011/04/14)
The invention provides antimicrobial compounds and compositions, and methods of using them. The compounds and compositions include, for example, a compound of any one of Formulas I-X. The invention further provides methods of preparing the compounds, and useful intermediates for their preparation. The compounds can possess highly specific and selective activity, such as antibacterial activity and/or enzymatic inhibitory activity. Accordingly, the compounds and compositions can be used to treat bacterial infections, or to inhibit or kill bacteria, either in vitro or in vivo.
Convenient preparation of N-maleoyl amino acid succinimido esters using N-trifluoroacetoxysuccinimide
Paterson, Michael J.,Eggleston, Ian M.
, p. 303 - 308 (2008/03/17)
One-pot cyclization and esterification of readily available maleamic acid derivatives using N-trifluoroacetoxysuccinimide provide a convenient and cost-effective route to a variety of useful N-maleoyl amino acid N-hydroxysuccinimido esters. Copyright Taylor & Francis Group, LLC.
Synthesis, anticholinesterase activity and structure-activity relationships of m-Aminobenzoic acid derivatives
Trujillo-Ferrara, Jose,Montoya Cano, Leticia,Espinoza-Fonseca, Michel
, p. 1825 - 1827 (2007/10/03)
The synthesis, acetylcholinesterase inhibitory capacity and structure-activity relationships of simple-structured m-Aminobenzoic acid derivatives are reported. Compound 1b was found to be more potent than galanthamine and tacrine in inhibiting acetylcholinesterase.
1H and 13C NMR spectra for a series of arylmaleamic acids, arylmaleimides, arylsuccinamic acids and arylsuccinimides
Trujillo-Ferrara, Jose,Santillan, Rosa,Beltran, Hiram I.,Farfan, Norberto,Hoepfl, Herbert
, p. 682 - 686 (2007/10/03)
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
Design, synthesis, and biochemical evaluation of N-substituted maleimides as inhibitors of prostaglandin endoperoxide synthases
Kalgutkar, Amit S.,Crews, Brenda C.,Marnett, Lawrence J.
, p. 1692 - 1703 (2007/10/03)
N-(Carboxyalkyl)maleimides are rapid as well as time-dependent inhibitors of prostaglandin endoperoxide synthase (PGHS). The corresponding N- alkylmaleimides were only time-dependent inactivators of PGHS, suggesting that the carboxylate is critical for rapid inhibition. Several N-substituted maleimide analogs containing structural features similar to those of the nonsteroidal anti-inflammatory drug aspirin were synthesized and evaluated as inhibitors of PGHS. Most of the aspirin-like maleimides inactivated the cyclooxygenase activity of purified ovine PGHS-1 in a time- and concentration-dependent manner similar to that of aspirin. The peroxidase activity of PGHS was also inactivated by the maleimide analogs. The cyclooxygenase activity of the inducible isozyme, i.e., PGHS-2, was also inhibited by these compounds. The corresponding succinimide analog of N-5- maleimido-2-acetoxy-1-benzoic acid did not inhibit either enzyme activity, suggesting that inactivation was due to covalent modification of the protein. The mechanism of inhibition of PGHS-1 by N-(carboxyheptyl)maleimide was investigated. Incubation of apoPGHS-1 with 2 equiv of N-(carboxyheptyl)[3,4- 14C]maleimide led to the incorporation of radioactivity in the protein, but no adduct was detected by reversed-phase HPLC, suggesting that it was unstable to the chromatographic conditions. Furthermore, hematin- reconstituted PGHS-1, which was rapidly inhibited by N- (carboxyheptyl)maleimide, displayed spontaneous regeneration of about 50% of the cyclooxygenase and peroxidase activities, suggesting that the adduct responsible for the inhibition breaks down to regenerate active enzyme. ApoPGHS-1, inhibited by N-(carboxyheptyl)maleimide, did not display regeneration of enzyme activity, but addition of hematin to the inhibited apoenzyme led to spontaneous recovery of about 50% of cyclooxygenase activity. These results suggest that addition of heme leads to a conformational change in the protein which increases the susceptibility of the adduct toward hydrolytic cleavage. ApoPGHS-1, pretreated with N(carboxyheptyl)maleimide, was resistant to trypsin cleavage, suggesting that the carboxylate functionality of the maleimide binds in the cyclooxygenase channel. A model for the interaction of N-(carboxyheptyl)maleimide in the cyclooxygenase active site is proposed.
INFLUENCE OF MEDIUM AND SUBSTITUENTS ON ACYLATION OF AROMATIC AMINES AND THEIR POLYMERIC ANALOGS WITH MALEIC ANHYDRIDE
Donya, A. P.,Pakter, M. K.,Sokhina, S. I.
, p. 2093 - 2097 (2007/10/02)
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.
Preparation and Characterization of Hetero-bifunctional Cross-linking Reagents for Protein Modifications
Kitagawa, Tsunehiro,Shimozono, Takuro,Aikawa, Tadaomi,Yoshida, Toyokichi,Nishimura, Haruki
, p. 1130 - 1135 (2007/10/02)
Ten aromatic and aliphatic cross-linking reagents of hetero-bifunctional type were synthesized as part of a search for useful reagents of this type.All of the reagents possess two selectively reactive groups a maleimide group which can combine with a thiol group via its double bond and an N-Hydroxysuccinimidyl ester (one of the most hydrophilic active esters), which can react with an ammmine group.It was found that the active esters of the reagents tested were mostly more reactive with lysine than with leucine, and acylated amino acids more rapidly at pH 8.0 than at pH 7.0.It was also found that the stability of the maleimide group in the compounds tested depends largely upon the pH of the buffer used.The most stable pH was 5.0-6.0.To use one of the present compounds as a cross-linker, the crystalline reagent should be dissolved in tetrahydrofuran of dioxane and the solution used for cross-linking.The acylation step should be carried out first with thiol addition to the maleimide group as the second step.The optimum pH of the buffer used for the first step is slightly basic.The reaction time should be limited to less than 1 hr.When the first step is over, the pH of the reaction mixture should be changed to 5.0-6.0.Keywords---cross-linker; hetero-bifunctional reagent; reactivity of N-hydroxy-succinimidyl ester; stability of maleimide residue; N-(maleimidobenzoyloxy)succinimide derivative; N-(maleimidoalkyloxy)succinimide derivative
