Ghashghaei, Ouldouz , Caputo, Samantha , Sintes, Miquel , Reves, Marc , Kielland, Nicola , Estarellas, Carolina , Luque, F. Javier , Avino, Anna , Eritja, Ramon , SERNA GALLEGO, ANA DEL ROSARIO, Antonio Marrugal-Lorenzo, Jose , Pachon, Jeronimo , Sanchez-Cespedes, Javier , Treadwell, Ryan , de Moliner, Fabio , Vendrell, Marc , Lavilla, Rodolfo
No
Chem.-Eur. J.
Article
Científica
1
1
5.16
25/09/2018
000445447400031
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-Bienayme reaction on a range of -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.
azines; biological activity; isocyanides; multicomponent reactions; novel scaffolds