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
Construction of a six-membered fused N-heterocyclic ring via a new 3-component reaction: synthesis of (pyrazolo)pyrimidines/pyridines
P. Mahesh Kumar,P. Mahesh Kumar,K. Siva Kumar,Pradeep K. Mohakhud,Khagga Mukkanti,Ravikumar Kapavarapu,Kishore V. L. Parsa,Manojit Pal +7 more
TL;DR: A conceptually new three-component reaction was developed to construct a six-membered fused N-heterocyclic ring affording (pyrazolo)pyrimidines/pyridines as potential inhibitors of PDE4.
Journal ArticleDOI
Convenient one-step synthesis of a medicinally relevant benzopyranopyridine system
Nikolai M. Evdokimov,Artem S. Kireev,Andrey A. Yakovenko,Mikhail Yu. Antipin,Mikhail Yu. Antipin,Igor V. Magedov,Alexander Kornienko +6 more
TL;DR: A three-component reaction of salicylaldehydes, thiols and 2 equiv of malononitrile that leads to the formation of a series of compounds incorporating 2,4-diamino-3-cyano-5-sulfanylbenzopyrano[2,3-b]pyridine framework is described.
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Tetrasubstituted furans by PdII/CuI-cocatalyzed three-component domino reactions of 2-(1-alkynyl)-2-alken-1-ones, nucleophiles and diaryliodonium salts
Wenbo Li,Junliang Zhang +1 more
TL;DR: A novel Pd(OAc)(2)/CuI-cocatalyzed three-component reaction of 2-(1-alkynyl)-2-alken-1-ones, nucleophiles and diaryliodonium salts has been developed, which allows the synthesis of tetrasubstituted furans in good to high yields under mild conditions.
Journal ArticleDOI
Recent advances in InCl3-catalyzed one-pot organic synthesis
Journal ArticleDOI
Three-component strategy toward 5-membered heterocycles from isocyanide dibromides.
TL;DR: New cascades were developed involving the addition of a nitrogenated nucleophile-an azide or a tetrazole-on isocyanide dibromides, an electrocyclization, and a Suzuki coupling, which afford new accesses to tetrazoles and triazole scaffolds.