Calix[n]arenos como sistemas de encapsulamento e plataforma para catalisadores assimétricos

• Autor(a) principal: Teixeira, Milena Galdino
• Data de Publicação: 2011
• Tipo de documento: Dissertação
• Idioma: por
• Título da fonte: LOCUS Repositório Institucional da UFV
• Texto Completo: http://locus.ufv.br/handle/123456789/2109
• topic: Calix[n]arenos; Sistemas de encapsulamento; Catalisadores assimétricos; Calix[n]arenes; Encapsulation systems; Asymmetric catalysts; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA

The supramolecular chemistry has evolved over the past three decades, and has been an extremely dynamic field and truly interdisciplinary. In this work was synthesize derivatives of p-tert-butylcalix[4 and 6]arene, in order to apply them as a platform for asymmetric ligands and carriers systems of isoniazid. First the synthesis of five derivatives of p-tert-butylcalix[4]arene linked to (R)- or (S)-1-phenylethylamine was described. The chiral ligands (3a-d e 4a) were obtained with total yields between from 4 to 16%. These compounds were tested as chiral ligands in the reaction addition of dietilzinco in benzaldehyde, however, enantiomeric excesses were not obtained. It also describes the synthesis of two hosts calix[n]arenes (1d and 8b) was described. These hosts, in addition to methyl-β-cyclodextrin (9) and 2-hydroxypropyl-β-cyclodextrin (10) were used as carriers systems of isoniazid (11), which is a drug used to treat tuberculosis, due to its high potency. Thus we decided to prepare and characterize molecular complexes between (11) and hosts (1d, 8b, 9 and 10) and test the biological activity of these complexes against Mycobacterium tuberculosis, by means of biologicals tests in vitro. The best results were obtained for the complex (1d:11) and (9:11) that presented a MIC of 1.7 nmol/mL. This result is equivalent to that obtained for pure isoniazid wich presents a MIC of 1.5 nmol/mL.