| Abstract
| - This study reports the synthesis of tetrahydrobenzo- (4−6) and benzopsoralen (7−9) derivativesobtained by condensing the fourth ring to the pyrone side of the tricyclic psoralen moiety. Thenew compounds are characterized by having a methoxy, a hydroxy, or a dimethylaminopropoxyside chain inserted at position 8 of the psoralen chromophore. The evaluation of thephotoantiproliferative activity on human tumor cell lines along with skin phototoxicity on guineapigs revealed an interesting photobiological pattern for the dimethylaminopropoxy derivatives6 and 9: they are in fact able to exert an antiproliferative effect up to 1 order of magnitudehigher than that of the well-known drug 8-MOP, but they are devoid of skin phototoxicity.The ability of both 6 and 9 to photoadd to DNA is demonstrated by the isolation andcharacterization of the 4‘,5‘-monoadducts. AM1 calculations were also performed to gain furtherinsight into the molecular basis of their photobiological behavior.
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