Synthesis of Amino and Ammonium Resorcin[4]arenes as Potential Receptors

Bruno Botta; Marco Pierini; Giuliano Delle Monache; Deborah Subissati; Fabiana Subrizi; Giovanni Zappia

doi:10.1055/s-2008-1067111

PAPER

Synthesis of Amino and Ammonium Resorcin[4]arenes as Potential Receptors

Bruno Botta*^a, Marco Pierini^a, Giuliano Delle Monache^a, Deborah Subissati^a, Fabiana Subrizi^a, Giovanni Zappia*^b
^a Dip. di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Sapienza Università di Roma, P.le A. Moro 5, 00185 Roma, Italy
Fax: +39(06)49912780; e-Mail: bruno.botta@uniroma1.it;
^b Istituto di Chimica Farmaceutica, Facoltà di Farmacia, Università di Urbino ‘Carlo Bo’, P.za del Rinascimento 6, 61029 Urbino, Italy
e-Mail: giovanni.zappia@uniurb.it ;

Abstract

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Abstract

Starting from the tetrabromide 1a (cone conformation) a number of resorcin[4]arene derivatives (3a, 4a, 5a, 6a) containing an amino function in the side chains have been prepared. Preliminary investigations, including UV, NMR, and MS analyses, of mixtures of the resorcinarene and its potential guests, such as metal cations or amino acids, evidenced promising new properties, depending on the nature of the substituents. Notably, treatment of 1a with pyridine gave readily the corresponding pyridinium salt 7a, capable of interacting with Ga(III) salts in aqueous solution. The same results have been obtained starting from the tetrabromide 1b (1,2-alternate conformation) for two of the above reactions, giving derivatives 3b and 7b.

Key words

macrocycles - molecular recognition - resorcinarenes - receptors - host-guest systems

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