Abstract
Ozonolysis of lapachol ( 1), resulting in an unusual formation of a potent antitumor agent 2-acetylfuranonaphthoquinone ( 3) along with the expected aldehyde 6, is described. The reaction of lapachol ( 1) with CAN in dry acetonitrile leading to biologically active furanonaphthoquinones is also reported. The antitumoral activity of the tested compounds on human DU-145 prostate carcinoma cells was evaluated following XTT assay. The results revealed that 2-(1-methylethenyl)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione ( 5), β-lapachone ( 10) and dehydro-β-lapachone diacetate ( 11) showed 100% inhibition at 25 μg/ml. All the tested samples showed dose-dependent activity.
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