Síntese, Biotransformação e Avaliação Biológica de Substâncias Policíclicas Cage-Like Derivadas do Aduto de Diels-Alder Triciclo[6.2.1.02,7]undeca-4,9-dien-3,6-diona

AUTOR(ES)

Felicia Megumi Ito

DATA DE PUBLICAÇÃO

2007

RESUMO

In this work it was performed the synthesis of polycyclic cage-like molecules by classical organic reactions and by biotransformation process in order to obtain potentially bioactive compounds from the Diels-Alder adduct trycyclo[6.2.1.0<2,7>]undeca-4,9-dien-3,6-dione. We obtained the compounds 7, 12, 15, 16, 28, 29, 30, 32, 34, 35a, 35b, 36, 37, 38 e 39 (look at the dissertation). The compounds 15, 32, 34, 35 and 35b are being reported for the first time. Among the tested compounds 7, 12, 15, 16, 28, 29, 30, 32, 34, 39 for cytotoxic activity, compound 34 showed cytotoxic towards HCT-8, SF-295 and MDA-MB 435 cell lines, with IC50 values of 6.68 (17.9), 7.58 (20.4) and 13.51 (36.3) μg/ mL (μM), respectively. Compound 28 showed moderate albeit unspecific cytotoxic towards HL-60, HCT-8 and MDA-MB 435 cell lines, with IC50 values of 11,34 (65.2), 13,62 (78.2) and 13,52 (77.7) μg/ mL (μM), respectively. The results revealed the absence of hemolytic activity for compound 7, 28, 30, 34 e 39 in mouse erythrocytes. The others compounds were not tested. Compounds 7, 12, 28, 29, 30 and 34 were tested for insecticidal activity and the results were quite promising as they caused significant mortality on insects of the species S. zeamais. Compounds 7, 12 and 28 were submitted to a biotransformation assays employing the saprobe fungus Mucor ramosissimus. As a result it was formed compounds 28 and 36 from 7. Compound 28 was obtained from biotransformation of 12. A mixture of isomers 12 and 37 was produced from compound 28. This compound was submitted to assays at different concentrations of spores (10<6>, 10<4>e 10<2>spores/ mL) and pH (4-9), leading to diastereomeric mixture of 12 and 37 with varied proportions.

ASSUNTO(S)

atividade citotóxica insecticide diels-alder hemólise cytotoxic activity biotransformation medicinal organic chemistry inseticida química orgânica medicinal hemolysis quimica organica diels-alder biotransformação

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