A New Multicomponent Reaction MCR4 for the Synthesis of Analogs of Staurosporine

Gelman, Mati; Massarano, Tlalit; Lavi, Ronit; Byk, Gérardo

doi:10.2174/1385272821666170817110101

Cited by 5 publications

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“…Atropoisomerism was observed in the HPLC of compounds with ortho‐substituted phenyl groups in position R 3 as previously shown . The ratio of atropoisomers in the mixtures were close to 1 : 1.…”

Section: Figuresupporting

confidence: 80%

“…We have recently developed a new MCR4 useful for generating chiral analogs of 3‐substituted isoindolinones, starting from tetramic acids as chiral precursors . Our strategy included the reaction in solution of substituted chiral tetramic acids which, together with an aldehyde, an isocyanide, a dienophile and a Lewis acid, that produced 3‐substituted isoindolinones in one pot according to the mechanism disclosed in Figure . Briefly, the high acidity of the tetramic acid methylene a , reacts with an aldehyde b in the presence of Ti(O‐iPr) 4 , producing a condensation intermediate c .…”

Section: Figurementioning

confidence: 99%

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Solid‐Phase Multicomponent Synthesis of 3‐Substituted Isoindolinones Generates New Cell‐Penetrating Probes as Drug Carriers

et al. 2020

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A modular solid‐phase multicomponent reaction for the synthesis of 3‐substituted isoindolinone derivatives has been carried out. A mixture of a chiral β‐keto lactam, an aldehyde, an isocyanide and a dienophile react to produce chiral 3‐substituted isoindolinones in one pot. Modularity was accomplished by using solid supported aldehydes and dienophiles. Optimization was achieved by using microwave as the source of energy. The reaction was also performed on a biologically relevant well‐known programed cell death‐inducing peptide D(KLAKLAK)2 on solid phase. The molecules show significant fluorescence with large Stokes shifts and fast cell penetration. The chimeric peptides can be tracked under a microscope thus proving the potential of the probes as cell sensors. They were efficiently internalized compared to unlabeled peptide, with a concomitant induction of programed cell death, thereby proving their potential as drug carriers.

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Section: Figuresupporting

confidence: 80%

Section: Figurementioning

confidence: 99%

Solid‐Phase Multicomponent Synthesis of 3‐Substituted Isoindolinones Generates New Cell‐Penetrating Probes as Drug Carriers

et al. 2020

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“…There is a potential use of CH-acids in Ugi-type reactions. For instance, tetramic acids have sussesfully been deployed in an isocyanide-based MCRs for synthesis of valuable heterocyclic compounds [ 54 , 55 ]. In this vein, Meldrum’s acid as privileged CH acid has meanwhile been applied as a surrogate to carboxylic acid in a Ugi-type reaction.…”

Section: Alternative Components For Carboxylic Acidsmentioning

confidence: 99%

Ugi Four-Component Reactions Using Alternative Reactants

Hooshmand

Zhang

2023

Molecules

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The Ugi four-component reaction (Ugi-4CR) undoubtedly is the most prominent multicomponent reaction (MCRs) that has sparked organic chemists’ interest in the field. It has been widely used in the synthesis of diverse heterocycle molecules such as potential drugs, natural product analogs, pseudo peptides, macrocycles, and functional materials. The Ugi-4CRs involve the use of an amine, an aldehyde or ketone, an isocyanide, and a carboxylic acid to produce an α-acetamido carboxamide derivative, which has significantly advanced the field of isocyanide-based MCRs. The so-called intermediate nitrilium ion could be trapped by a nucleophile such as azide, N-hydroxyphthalimide, thiol, saccharin, phenol, water, and hydrogen sulfide instead of the original carboxylic acid to allow for a wide variety of Ugi-type reactions to occur.β In addition to isocyanide, there are alternative reagents for the other three components: amine, isocyanide, and aldehyde or ketone. All these alternative components render the Ugi reaction an aptly diversity-oriented synthesis of a myriad of biologically active molecules and complex scaffolds. Consequently, this review will delve deeper into alternative components used in the Ugi MCRs, particularly over the past ten years.

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“…A related tandem Knoevenagel/double cycloaddition reaction was developed by Byk to obtain staurosporine analogues ( 824 ) [ 267 ]. This multicomponent reaction begins with the condensation of aldehyde ( 81 ) and substituted chiral tetramic acid ( 821 ), which under the reaction conditions suffer successive cycloadditions with an isocyanide ( 31 ) and a dienophile ( 823 ) to give the desired isoindoles (Scheme 175 ).…”

Section: Cycloaddition Reactions Of Isocyanidesmentioning

confidence: 99%

Stefano Marcaccini: a pioneer in isocyanide chemistry

et al. 2023

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Stefano Marcaccini was one of the pioneers in the use of isocyanide-based multicomponent reactions in organic synthesis. Throughout his career at the University of Florence he explored many different faces of isocyanide chemistry, especially those geared towards the synthesis of biologically relevant heterocycles. His work inspired many researchers who contributed to other important developments in the field of multicomponent reactions and created a school of synthetic chemists that continues today. In this manuscript we intend to review the articles on isocyanide multicomponent reactions published by Dr. Marcaccini and analyse their influence on the following works by other researchers. With this, we hope to highlight the immense contribution of Stefano Marcaccini to the development of isocyanide chemistry and modern organic synthesis as well as the influence of his research on future generations. We believe that this review will not only be a well-deserved tribute to the figure of Stefano Marcaccini, but will also serve as a useful inspiration for chemists working in this field. Graphical abstract

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A New Multicomponent Reaction MCR4 for the Synthesis of Analogs of Staurosporine

Cited by 5 publications

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Solid‐Phase Multicomponent Synthesis of 3‐Substituted Isoindolinones Generates New Cell‐Penetrating Probes as Drug Carriers

Solid‐Phase Multicomponent Synthesis of 3‐Substituted Isoindolinones Generates New Cell‐Penetrating Probes as Drug Carriers

Ugi Four-Component Reactions Using Alternative Reactants

Stefano Marcaccini: a pioneer in isocyanide chemistry

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