Tetrahydroisoquinoline Alkaloids

Antitumor natural products belonging to the tetrahydroisoquinoline family have been under study for the last 30 years, starting with the isolation of napthyridi-nomycin.46 They normally bind to DNA by alkylation of specific nucleotide sequences in the minor groove. Most of these alkaloids contain quinone moieties and act by reductive alkylation mechanisms and also by generation of oxygen radicals via their one-electron reduction to a semiquinone species. The presence of either a nitrile or a hydroxy group on the position of the pyrazine ring a to the isoquinoline nitrogen is essential for DNA alkylation, which involves the generation of an intermediate iminium species.

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