2024-03-28T11:50:58Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/348562011-04-24T22:00:00Zcom_10261_100com_10261_5col_10261_353
New acyclic receptors containing pyridazine units. The influence of pi-stacking on the selective transport of lipophilic phenethylamines
Campayo, Lucrecia
Calzado, Fabián
Cano, M. Carmen
Yunta, María J. R.
Pardo, Mercedes
Navarro, Pilar
Jimeno, M. Luisa
Gómez-Contreras, Fernando
Sanz, Ana M.
Pyridazine receptors
Lipophilic phenethylamines carriers
Abstract—The synthesis of four new series of acyclic heteroaromatic receptors is described. They are built by two flexible polyether chains
functionalised at their end with pyridazinone or methylpyridazine rings and connected by pyridine or benzene units. Their ability as carriers
of lipophilic and hydrophilic phenethylamines and metallic cations has been evaluated. Transport rates show that, in general, these compounds are much more efficient carriers of lipophilic amines than of dopamine and NaC,KC and Ca2C ions. Their transport selectivities
towards phenethylamine and homoveratrylamine are discussed on the basis of their structural features. Molecular modelling studies suggest
that interaction of the aromatic moiety of the guest with the pyridazinone rings via double p-stacking, or with the pyridine ring by single
p-stacking, should be responsible of their enhanced efficacy and selectivity in the transport of lipophilic phenethylamines.
2011-04-25T07:28:09Z
2011-04-25T07:28:09Z
2005
artículo
Tetrahedron 61 : 11965–11975 (2005)
0040-4020
http://hdl.handle.net/10261/34856
10.1016/j.tet.2005.09.069
eng
http://dx.doi.org/10.1016/j.tet.2005.09.069
closedAccess
Elsevier