Synthesis and antitumor activity of some new xanthotoxin derivatives

The condensation of 4-amino-9-methoxy psoralene (4-aminoxanthotoxin) with some aromatic aldehydes led to the formation of 4-arylimine xanthotoxin derivatives 2a-h, which were cyclized with mercaptoacetic acid to afford the thiazolidinone derivatives 3a-h. On the other hand, the reaction of aminoxanthotoxin 1 with some anhydrides afforded 4-imidione derivatives 3a-d. When 1 reacted with some isothiocyanates, the thiourea derivatives 5a-c were obtained but the thiourea derivative 6 was obtained when 1 reacted with ammonium thiocyanate. The thiourea derivative 6 was cyclized by the reaction with monochloroacetic acid in the presence of sodium acetate to give aminothiazolidinone derivative 7, but when the same reaction is carried out in the presence of pyridine, the thioxoimidazolidinone 8 was formed. The condensation of xanthotoxin sulphonamide with aromatic aldehydes gave the aryliminosulphonyl derivatives 9a-e. Xanthotoxin sulphonyl hydrazine condensed with some anhydride afforded sulphonic acid imide derivatives 10a-c. The antitumor and cytotoxic activities of 9 synthesized derivatives were tested, five compounds were found to be active, they inhibited the growth of HeLa cells. (C) 2009 Elsevier Masson SAS. All rights reserved.