Multiple Multicomponent Reactions: Unexplored Substrates, Selective Processes, and Versatile Chemotypes in Biomedicine

Multiple multicomponent reactions rapidly assemble complex structures. Despite being very productive, the lack of selectivity and the reduced number of viable transformations restrict their general application in synthesis. Hereby, we describe a rationale for a selective version of these processes b...

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Detalles Bibliográficos
Autores: Ghashghaei, Ouldouz, Caputo, Samantha, Sintes, Miquel, Revés, Marc, Kielland, Nicola, Estarellas, Carolina, Luque, F. Javier, Aviñó, Anna, Eritja Casadellà, Ramón, Serna, Ana, Marrugal-Lorenzo, José Antonio, Pachón, Jerónimo, Sánchez-Céspedes, Javier, Treadwell, Ryan, De Moliner, Fabio, Vendrell, Marc, Lavilla, Rodolfo
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2018
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/170288
Acceso en línea:http://hdl.handle.net/10261/170288
Access Level:acceso abierto
Palabra clave:Azines
Biological activities
Isocyanides
Multicomponent reactions
Novel scaffolds
Descripción
Sumario:Multiple multicomponent reactions rapidly assemble complex structures. Despite being very productive, the lack of selectivity and the reduced number of viable transformations restrict their general application in synthesis. Hereby, we describe a rationale for a selective version of these processes based in the preferential generation of intermediates which are less reactive than the initial substrates. In this way, applying the Groebke–Blackburn–Bienaymé reaction on a range of α-polyamino-polyazines, we prepared a family compact heterocyclic scaffolds with relevant applications in medicinal and biological chemistry (live cell imaging probes, selective binders for DNA quadruplexes, and antiviral agents against human adenoviruses). The approach has general character and yields complex molecular targets in a selective, tunable and direct manner. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim