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A Web Tool for Generating High Quality Machine-readable Biological Pathways
Published on: February 8, 2017
Charting the Chemical Reaction Space around a Multicomponent Combination: Controlled Access to a Diverse Set of
Pau Nadal Rodríguez1, Ouldouz Ghashghaei1, Anna M Schoepf1
1Department of Medicinal Chemistry, Faculty of Pharmacy and Food Sciences, University of Barcelona and Institute of Biomedicine UB (IBUB), Av. De Joan XXIII, 27-31, 08028, Barcelona, Spain.
Abstract:
Charting the chemical reaction space around the combination of carbonyls, amines, and isocyanoacetates allows the description of new multicomponent processes leading to a variety of unsaturated imidazolone scaffolds. The resulting compounds display the chromophore of the green fluorescent protein and the core of the natural product coelenterazine. Despite the competitive nature of the pathways involved, general protocols provide selective access to the desired chemotypes. Moreover, we describe unprecedented reactivity at the C-2 position of the imidazolone core to directly afford C, S, and N-derivatives featuring natural products (e.g. leucettamines), potent kinase inhibitors, and fluorescent probes with suitable optical and biological profiles.
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