Synthesis of several new 5-amino-substituted derivatives of 5-amino-6H-imidazo[4,5,1-de]-acridin-6-one bearing in the benzene ring OH, OCH3, CH3, tert-butyl, or OCH2O groups is described. 8-OH-substituted compounds or double-substituted 7-OH-10-OCH3 compounds demonstrated potent in vivo activity against murine P388 leukemia. The highest activity was exhibited by 5-[[2-[[2-(diethylamino)ethyl]amino]ethyl]amino]-8-hydroxy-6H- imidazo[4,5,1-de]-acridin-6-one (4c).
The synthesis of substituted chalcones, thioflavanones, and thioflavones hydroxylated in both A
and B rings is described. Acetoquinone (1) was transformed into 2,5-dihydroxy-6-(p-methoxybenzylmercapto)acetophenone (2) and subsequently into its 2,5-dimethoxy (3) and 2,5-dibenzyloxy (4)
derivatives. Compounds 3 and 4 were condensed with suitable benzaldehydes to give chalcones
5−10. The thiol group of the chalcones was deprotected by a cleavage of the p-methoxybenzyl
protecting group using a new, mild method (silver nitrate in boiling ethanol, 2 h), and the products
were cyclized to thioflavanones (15−20). Dehydrogenation of the thioflavanones gave related
thioflavones (25−27). Deprotection of methoxy and benzyloxy groups is also described.
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