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
Cascade synthesis of selective dihydro pyridazino fused acridinone derivatives via MCM-41 catalyzed ring-opening/ring-closure reaction
TL;DR: An enhanced one-pot synthesis of new functionalized 5,6-dihydro-5,5-dimethyl-2-phenyl-2 H -pyridazino[3,4,5]-acridin-1(4 H )-one derivatives with different substituted patterns by using mesoporous MCM-41 catalyst via a ring opening/ring closure reaction process has been established.
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Regioselective Passerini and Passerini–Knoevenagel Reactions with vic‐Diketo Amides
TL;DR: The Passerini reaction of vic-diketo amides with a variety of isocyanides and carboxylic acids has been examined in this article, where α-Acyloxy β-keto carboxamides were formed regioselectively as the major products.
Journal ArticleDOI
Solvent‐free Synthesis of 1,8‐Dioxo‐octahydroxanthenes and Tetra‐hydrobenzo[a]xanthene‐11‐ones over Poly(N,N′‐dibromo‐N‐ethylnaphtyl‐2,7‐sulfonamide)
TL;DR: In this paper, poly(N,N′-dibromo-N-ethylnaphtyl-2,7-sulfonamide) (PDNES) was applied for the synthesis of 1,8-dioxo-octahydroxanthenes and tetra-hydrobenzo[a]xanthene-11-ones under neutral and solvent-free conditions.
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Sc(OTf)3 catalysed multicomponent synthesis of chromeno[2,3-d]pyrimidinetriones under solvent-free condition
TL;DR: An efficient, simple, and environmentally friendly synthesis of a series of chromeno[2,3d]pyrimidine-trione derivatives has been accomplished via the three-component reaction of a barbituric acid as mentioned in this paper.
Journal ArticleDOI
Synthesis of diverse phenylglycine derivatives via transformation of Ugi four-component condensation primary adducts
TL;DR: In this article, a synthetically useful post-condensation transformation of Ugi four-component condensation primary adducts is described for the first time, which can be regarded as the enediamine tautomers of the Ugi 4-component CPA between 2-formylbenzoic acids, arylamines and isocyanides.