Several derivatives of 2,2':5',2''-terthiophene, 1a, and a structural analogue of this natural phototoxin, i.e. 5-[4-(1,2-methylenedioxy)phenyl]-2,2'-bithiophene, 2, have been conveniently synthesized on a medium scale using a general approach which involves palladium-catalyzed carbon-carbon bond forming reactions between (hetero)aryl halides and heteroaryl organometallics such as Grignard reagents, organozinc and organotin compounds. These 2,2':5',2''-terthiophene derivatives, which include some naturally-occurring compounds, have been characterized by EIMS spectrometry, H-1 and C-13 NMR spectroscopy as well as by absorption and fluorescence measurements. Four of these phototoxins exhibit considerable antibiotic and antiviral properties in the presence of UVA light and are cytotoxic against the P 815 mouse mastocytoma cell line.
Synthesis and characterization of 2,2':5',2"-terthiophene derivatives of possible therapeutic use
ROSSI, RENZO;CARPITA, ADRIANO;
1990-01-01
Abstract
Several derivatives of 2,2':5',2''-terthiophene, 1a, and a structural analogue of this natural phototoxin, i.e. 5-[4-(1,2-methylenedioxy)phenyl]-2,2'-bithiophene, 2, have been conveniently synthesized on a medium scale using a general approach which involves palladium-catalyzed carbon-carbon bond forming reactions between (hetero)aryl halides and heteroaryl organometallics such as Grignard reagents, organozinc and organotin compounds. These 2,2':5',2''-terthiophene derivatives, which include some naturally-occurring compounds, have been characterized by EIMS spectrometry, H-1 and C-13 NMR spectroscopy as well as by absorption and fluorescence measurements. Four of these phototoxins exhibit considerable antibiotic and antiviral properties in the presence of UVA light and are cytotoxic against the P 815 mouse mastocytoma cell line.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
