Charting the Chemical Reaction Space around a Multicomponent Combination: Controlled Access to a Diverse Set of Biologically Relevant Scaffolds.

Autor: Nadal Rodríguez P; Department 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., Ghashghaei O; Department 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., Schoepf AM; Department 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., Benson S; Centre for Inflammation Research, The University of Edinburgh, Edinburgh, UK., Vendrell M; Centre for Inflammation Research, The University of Edinburgh, Edinburgh, UK., Lavilla R; Department 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.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2023 Oct 09; Vol. 62 (41), pp. e202303889. Date of Electronic Publication: 2023 Jun 02.
DOI: 10.1002/anie.202303889
Abstrakt: 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.
(© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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