TY - JOUR
T1 - Charting the Chemical Reaction Space around a Multicomponent Combination: Controlled Access to a Diverse Set of Biologically Relevant Scaffolds
AU - Nadal rodríguez, Pau
AU - Ghashghaei, Ouldouz
AU - Schoepf, Anna M.
AU - Benson, Sam
AU - Vendrell, Marc
AU - Lavilla, Rodolfo
N1 - Funding Information:
We warmly thank Profs. G. Fabriàs, J. B. Blanco, A. Shafir, I. Alfonso, J. L. Abad (IQAC, CSIC, Barcelona) and Dr. L. Mendive‐Tapia (U. Edinburgh) for useful suggestions and support. S.B. and M.V. acknowledge funding from EPSRC (EP/W015706/1) and an ERC Consolidator Grant (DYNAFLUORS, 771443). Funding from Ministerio de Ciencia e Innovación (Spain) and the European Regional Development Fund (EDFR) (PID2019‐107991RB‐I00) is gratefully acknowledged. P.N.R. thanks Ministerio de Ciencia e Innovación (Spain) for a predoctoral grant. A.M.S. thanks the Austrian Science Fund (FWF): Project J4541‐N. O.G. and M.V. thank Eurolife (Network of European Universities in Life Sciences) for the support through the Eurolife Postdoc Mobility and Knowledge Exchange program.
Publisher Copyright:
© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
PY - 2023/5/16
Y1 - 2023/5/16
N2 - 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.
AB - 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.
U2 - 10.1002/anie.202303889
DO - 10.1002/anie.202303889
M3 - Article
SN - 1433-7851
JO - Angewandte Chemie International Edition
JF - Angewandte Chemie International Edition
ER -