Synthesis and characterization of new methylpsoralens as potential photochemotherapeutic agents.
Three new psoralens with methyl groups on carbons involved in their reactive double bonds (compounds 9-11 in Scheme 1) were synthesized from the corresponding 7-hydroxycoumarins by cyclization of acetonyl derivatives of the latter in an alkaline medium. In preliminary tests, the new methyl-substituted psoralens exhibited considerable interaction in the dark with DNA, good photoreactivity against the macromolecule, and also interesting antiproliferative activity.
Antonello
C
C
Dipartimento di Scienze Farmaceutiche, University of Padova, Italy.
Zagotto
G
G
Mobilio
S
S
Marzano
C
C
Gia
O
O
Uriarte
E
E
D000818:Animals; D002286:Carcinoma, Ehrlich Tumor / Q000378:metabolism; D002455:Cell Division / Q000187:drug effects; D003432:Cross-Linking Reagents / Q000494:pharmacology; D004247:DNA / Q000737:chemistry / Q000187:drug effects; D004273:DNA, Neoplasm / Q000096:biosynthesis; D017484:Dermatitis, Phototoxic / Q000188:drug therapy / Q000473:pathology; D011564:Furocoumarins / Q000138:chemical synthesis* / Q000494:pharmacology; D006168:Guinea Pigs; D009682:Magnetic Resonance Spectroscopy; D008730:Methoxsalen / Q000494:pharmacology; D051379:Mice; D008815:Mice, Inbred Strains; D010777:Photochemistry; D010778:Photochemotherapy; D013055:Spectrophotometry, Infrared; D014407:Tumor Cells, Cultured
D003432:Cross-Linking Reagents; D004273:DNA, Neoplasm; D011564:Furocoumarins; D004247:DNA; D008730:Methoxsalen