Premium
Multiple Multicomponent Reactions: Unexplored Substrates, Selective Processes, and Versatile Chemotypes in Biomedicine
Author(s) -
Ghashghaei Ouldouz,
Caputo Samantha,
Sintes Miquel,
Revés Marc,
Kielland Nicola,
Estarellas Carolina,
Luque F. Javier,
Aviñó Anna,
Eritja Ramón,
SernaGallego Ana,
MarrugalLorenzo José Antonio,
Pachón Jerónimo,
SánchezCéspedes Javier,
Treadwell Ryan,
de Moliner Fabio,
Vendrell Marc,
Lavilla Rodolfo
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802877
Subject(s) - biomedicine , combinatorial chemistry , nanotechnology , dna , chemistry , chemotype , computational biology , biology , materials science , bioinformatics , biochemistry , chromatography , essential oil
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.