Synthesis and NMR study of a first generation dendrimer having four branches involving four glycine and one carbomoyl-(3,7-dimethoxy-2-naphthalene) groups and attempts to complex it with α-, β- or γ-cyclodextrins

The synthesis of benzene-1, 4-bis(carboxamido-N,N-bis(acetyldiglicylglycinamide-N'-ethyl-2-N"-carbomoyl-(3,7-dimethoxy-2-naphthalene) by the method allowing one to avoid its tedious purification and unsuccessful attempts to obtain its quadruple complexes with native cyclodextrins are described. Molecular modeling of diglicylglycinamide-N-ethyl-2-N"-carbomoyl-(3,7-dimethoxy-2-naphthalene) mimicking a dendrimer branch indicated that the complexes should form. However, no manifestations of the complexation could be detected in NMR spectra and chromatographic measurements. Molecular modeling of the dendrimer itself have shown that the pair-wise stacking of the aromatic end groups could be responsible for the lack of the complexation. (C) 2004 Elsevier B.V. All rights reserved.