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
A simple and efficient approach to the synthesis of 4H-furo[3,4-b]pyrans via a three-component reaction of isocyanides
TL;DR: A three-component reaction of an isocyanide, a dialkyl acetylenedicarboxylate, and tetronic acid in dichloromethane at room temperature afforded 4H-furo[3,4-b]pyran derivatives which have a broad spectrum of biological activity.
Journal ArticleDOI
Microwave-assisted synthesis of pyrazolo[3,4-d]pyrimidines from 2-amino-4,6-dichloropyrimidine-5-carbaldehyde under solvent-free conditions
Jairo Quiroga,Jorge Trilleras,Braulio Insuasty,Rodrigo Abonia,Manuel Nogueras,Antonio Marchal,Justo Cobo +6 more
TL;DR: The microwave-induced synthesis of pyrazolo[3,4d]pyrimidines 4 in the reaction of N4substituted-2,4-diamino-6-chloro-5-carbaldehydes 3 with hydrazine is described in this paper.
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An Efficient Tetrabutylammonium Fluoride (TBAF)‐Catalyzed Three‐Component Synthesis of 3‐Substituted Indole Derivatives under Solvent‐Free Conditions
TL;DR: In this paper, an efficient one-pot three-component synthesis of 3-substituted indoles has been developed by the reaction of indoles, active methylene compounds and aldehydes using a catalytic amount of tetrabutylammonium fluoride under solvent-free conditions.
Journal ArticleDOI
Nano-sio2: a green, efficient, and reusable heterogeneous catalyst for the synthesis of quinazolinone derivatives
TL;DR: In this article, a green and reusable nano-SiO2 catalyst was used for the multicomponent synthesis of quinazolinone derivatives from cyclocondensation of aromatic aldehydes and dimedone with 2-amino benzimidazole or 3amino-1,2,4-triazole.
Journal ArticleDOI
Chiral Brønsted Acid Catalyzed Enantioselective Addition of α-Isocyanoacetamides to Aldehydes
TL;DR: A clean and highly efficient enantioselective addition of alpha-isocyanoacetamides to aliphatic aldehydes catalyzed by chiral phosphoric acid in the presence of MS 5 A in toluene at -40 degrees C was developed.