Synthesis of new calix[4]arenes containing nucleoside bases

A family of novel calix[4]arene derivatives containing nucleoside bases were designed and synthesized. Coupling reaction between para mono- or bis-amino calix[4]arenes , or and thymin-1-ylacetic acid in the presence of DCC afforded mono- or bis-thymine-substituted calix[4]arenes , or in over 70% yield. Owing to the low solubility of adenine-N9-ylacetic acid in DMF and DMSO and the weak nucleophilicity of aminocalix[4]arene derivatives, alternatively, the substitution reaction of bromoacetylated aminocalix[4]arenes derivatives , , with adenine in the presence of sodium hydride was carried out to synthesize mono- or bis-adenine-substituted calix[4]arenes. Two kinds of isomers and or and were obtained due to the non-regiospecific alkylation of adenine, and their structures have been confirmed by 13C NMR and 1H NMR spectra.