N-METHYL AND O-METHYL DERIVATIVES OF 5,10-TETRAHYDROBENZO[G]ISOQUINOLINE-3,5,10-TRIONES

Some 5,10-tetrahydrobenzo[g]isoquinoline-3,5,10-triones 2 were prepare d by a Diels-Alder reaction between different 2-azadienes 1 and 1,4-na phthoquinone. The corresponding N- and O-methyl derivatives 3 and 4 re spectively were obtained by the use of CH3I in a basic medium: triethy lamine (method A), K2CO3 and tris[2-(2-methoxyethoxy)ethylamine] (meth od B) or in the presence of Ag2O. The reaction of N-methylation was re giospecific, while the O-methylation was regioselective. - The in vitr o cytotoxic activity of the prepared compounds was evaluated against m urine L 1210 leukemia cells and a human tumor cell line MDA-MB 231. A weak, not significant activity was observed (IC50 values are ranging f rom 6 to > 10 mug/ml).