Formation of octaalkylated rctt tetranaphthyl-resorcinarene derivatives containing biologically active components

Abstract

Derivatives containing eight easily transformable ester (2) or alkynyl (3) groups were prepared by the alkylation of rctt ortho-methyl-tetra-C-naphthyl-resorcinarene 1 with ethyl 2-bromoacetate and propargyl bromide. Amination of compound 2 gave conjugates (5, 6) of resorcinarenes with biologically active benzyl- and phenethylamines. The reactions proceeded most efficiently in a microwave reactor. The catalytic cycloaddition of benzyl azide or ethyl azidoacetate to octaalkynyl-resorcinarene 3 was used to prepare rctt resorcinarenes (7, 8) conjugated to eight triazole moieties. Resorcinarene 2 is easily converted to octacarboxy derivative (4), which reacts with ethanolamine and phenethylamine to give water-soluble salts (9, 10), whereas reactions with benzylamine and tryptamine result in the formation of complexes (11, 12) containing several amine groups arranged in space in different ways.