2018
DOI: 10.1007/s10593-018-2240-z
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3,4-Disubstituted maleimides: synthesis and biological activity

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Cited by 34 publications
(13 citation statements)
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“…In this article, we make for the first time a systematic study of the impact of DES choline chloride/ p -toluenesulfonic acid ChCl/TsOH and DES choline chloride/ p -toluenesulfonic acid–water ChCl/TsOH/H 2 O in the aza-Michael addition of arylamines 2 to maleimide 1 to obtain aminopyrrolidine-2,5-dione derivatives 3 under very mild reaction conditions with high yield. The derivatives are of great importance in biology, materials science, and chemistry; they are used as synthetic blocks to obtain small bioactive molecules, natural products, drugs, and agrochemicals. This contribution complements our previous work on nucleophilic addition reactions in α,β-unsaturated carbonyl compounds (maleimide and maleic anhydride) that were made in terms of the local hard and soft acid and base principle and the density functional theory. Now, our experimental and theoretical studies on the aza-Michael addition have been motived for two overarching goals: (i) development of a new experimental methodology under mild reaction conditions for fast and efficient synthesis of 3 , through the aza-Michael additions of 2 to 1 using ChCl/TsOH and water as solvents without the need of a catalyst, ligand, and/or additive and (ii) understanding the kinetics and thermodynamics of the interactions between ChCl/TsOH and the reagents and the effect of water on the supramolecular network of ChCl/TsOH using spectroscopic techniques and a potential energy surface.…”
Section: Introductionmentioning
confidence: 85%
“…In this article, we make for the first time a systematic study of the impact of DES choline chloride/ p -toluenesulfonic acid ChCl/TsOH and DES choline chloride/ p -toluenesulfonic acid–water ChCl/TsOH/H 2 O in the aza-Michael addition of arylamines 2 to maleimide 1 to obtain aminopyrrolidine-2,5-dione derivatives 3 under very mild reaction conditions with high yield. The derivatives are of great importance in biology, materials science, and chemistry; they are used as synthetic blocks to obtain small bioactive molecules, natural products, drugs, and agrochemicals. This contribution complements our previous work on nucleophilic addition reactions in α,β-unsaturated carbonyl compounds (maleimide and maleic anhydride) that were made in terms of the local hard and soft acid and base principle and the density functional theory. Now, our experimental and theoretical studies on the aza-Michael addition have been motived for two overarching goals: (i) development of a new experimental methodology under mild reaction conditions for fast and efficient synthesis of 3 , through the aza-Michael additions of 2 to 1 using ChCl/TsOH and water as solvents without the need of a catalyst, ligand, and/or additive and (ii) understanding the kinetics and thermodynamics of the interactions between ChCl/TsOH and the reagents and the effect of water on the supramolecular network of ChCl/TsOH using spectroscopic techniques and a potential energy surface.…”
Section: Introductionmentioning
confidence: 85%
“…The reaction between maleic anhydride and the primary amine successfully afforded probe 1 . 32 However, such a strategy did not work for the preparation of probes 2–4 , which contain 7-aminocoumarin scaffolds. Alternatively, 7-((2-bromoethyl)amino)-coumarin 2b and the alkylated products (methylated 3a and ethylated 4a ) were first constructed by substitution reactions.…”
Section: Resultsmentioning
confidence: 99%
“…Indole and maleimide moieties are present in the biologically active natural product and FDA-accepted drugs, making them appropriate for G4 targeting. , Bisindolylmaleimide ( BIM ) scaffold, consisting of indole and maleimide moieties, is found in several lead molecules that act as protein kinase C inhibitors . Herein, we have designed and synthesized a new class of trialkylated - BIM ligands (Figure ).…”
Section: Resultsmentioning
confidence: 99%