Síntese e avaliação da atividade antimalárica de novos ozonídeos

Abstract

The [3+4] cycloaddition reaction between different dienes (cyclopentadiene, 2-methylfurane and furane) and haloketones formed their corresponding cycloadducts. Ozonolysis of the cycloadducts yielded the ozonides 3α,5α-dimethyl-8,9,10-trioxatricyclo[5.2.1.12'6] undecan-4-one (6), 2,3α,5α-trimethyl-8,9,10,11-tetraoxatricyclo[5.2.1.1 2,6]undecan-4-one (9), 2,3β,5β-trimethyl-8,9,10,11-tetraoxatricyclo[5.2.1.1 2,6]undecan-4-one (10, exo isomer), 2,3β, 5β-trimethyl-8,9,10,11-tetraoxatricyclo[5.2.1.12,6]undecan- 4-one (11, endo isomer), 3α-isopropyl-8,9,10,11-tetraoxatricyclo[5.2.1.12,6]undecan- 4-one (14). The antimalaria activity of the ozonides was evaluated in vitro against strain of Plasmodium falciparum, from Thailand.