Journal ArticleDOI
"Multi-component reactions : emerging chemistry in drug discovery" 'from xylocain to crixivan'.
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TLDR
This review details developments of new, highly atom-economic MCR derived chemical methods, which enable the fast and efficient production of chemical libraries comprised of a variety of biologically relevant templates, and focuses on applications of isocyanide based MCR (IMCR) reactions.Abstract:
With the recent emergence of combinatorial chemistry and high-speed parallel synthesis for drug discovery applications, the multi-component reaction (MCR) has seen a resurgence of interest. Easily automated one-pot reactions, such as the Ugi and Passerini reactions, are powerful tools for producing diverse arrays of compounds, often in one step and high yield. Despite this synthetic potential, the Ugi reaction is limited by producing products that are flexible and peptide-like, often being classified as 'non drug-like'. This review details developments of new, highly atom-economic MCR derived chemical methods, which enable the fast and efficient production of chemical libraries comprised of a variety of biologically relevant templates. Representative examples will also be given demonstrating the successful impact of MCR combinatorial methods at different stages of the lead discovery, lead optimization and pre-clinical process development arenas. This will include applications spanning biological tools, natural products and natural product-like diversity, traditional small molecule and 'biotech' therapeutics respectively. In particular, this review will focus on applications of isocyanide based MCR (IMCR) reactions.read more
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Journal ArticleDOI
La2O3/TFE: An efficient system for room temperature synthesis of Hantzsch polyhydroquinolines
TL;DR: In this article, Lanthanum oxide (La2O3) in combination with 2,2,2-trifluoroethanol (TFE) was found to be an efficient system for the one-pot, four component synthesis of Hantzsch polyhydroquinoline derivatives from aromatic aldehydes, dimedone, ethyl acetoacetate and ammonium acetate at ambient temperature.
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Sc(OTf)3-catalyzed, solvent-free domino synthesis of functionalized pyrazoles under controlled microwave irradiation
TL;DR: An efficient, rapid, and green synthesis of functionalized pyrazoles has been accomplished under solvent-free conditions by the reaction of phenyl hydrazine, aldehydes and ethyl acetoacetate.
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Synthesis of novel fluorescent benzo[ a ]pyrano[2,3- c ]phenazine and benzo[ a ]chromeno[2,3- c ]phenazine derivatives via facile four-component domino protocol
TL;DR: An efficient and practical route to novel fluorescent benzo[a]pyrano[2,3-c]phenazine framework has been developed by one-pot, four-component reaction of 2-hydroxynaphthalene-1,4-dione, 1,2-phenylenediamines, aromatic aldehydes, and Meldrum's acid in glacial acetic acid at 70°C.
Journal ArticleDOI
Multicomponent Combinatorial Development and Conformational Analysis of Prolyl Peptide-Peptoid Hybrid Catalysts: Application in the Direct Asymmetric Michael Addition
Alexander F. de la Torre,Daniel G. Rivera,Daniel G. Rivera,Marco A. B. Ferreira,Arlene G. Corrêa,Márcio W. Paixão +5 more
TL;DR: The catalytic behavior of the peptide-peptoid hybrids was assessed in the asymmetric conjugate addition of aldehydes to nitroolefins, where most of the catalysts showed great efficacy and rendered the Michael adducts with good to excellent enantio- and diastereoselectivity.
Journal ArticleDOI
Novel multi-component synthesis of 1,4-disubstituted pyrrolo[1,2-a]quinoxalines through palladium-catalyzed coupling reaction/hetero-annulation in water
TL;DR: In this paper, 1,4-disubstituted pyrrolo[1,2-a ]quinoxalines were prepared through the one-pot multi-component reactions of 3-substitized-2-chloroquinox alines, propargyl alcohol, and secondary amines, catalyzed by Pd/Cu, in the presence of K 2 CO 3 and sodium dodecyl sulfate (SDS) in water.