The synthesis of new planar benzo[3',2':5,6]thiopyrano[4,3-d]pyrimidine derivatives, carrying different side groups in the 2 position, is described. The novel substituted pyrimidines were obtained by reaction of the key intermediate 3-dimethylamino methylen-7-methoxy-2,3-dihydrobenzo[3',2':5,6]thiopyran-4(4H)-one, characterized by a reactive group adjacent to the C=O function, with the suitable binucleophile amidines in a basic medium. All the new compounds were evaluated for the antiproliferative ability by an in vitro assay on two human tumour cell lines (HL-60 and HeLa), and the 2-phenyl substituted derivative showed the capacity to inhibit cell growth on HL-60. Linear flow dichroism measurements indicated the inability to form a molecular complex with DNA.
Synthesis and in vitro Antiproliferative Activity of New Substituted Benzo[3',2':5,6]thiopyrano[4,3-d]pyrimidines
MARINI, ANNA MARIA;DA SETTIMO PASSETTI, FEDERICO;SALERNO, SILVIA;LA MOTTA, CONCETTINA;SIMORINI, FRANCESCA;TALIANI, SABRINA;
2008-01-01
Abstract
The synthesis of new planar benzo[3',2':5,6]thiopyrano[4,3-d]pyrimidine derivatives, carrying different side groups in the 2 position, is described. The novel substituted pyrimidines were obtained by reaction of the key intermediate 3-dimethylamino methylen-7-methoxy-2,3-dihydrobenzo[3',2':5,6]thiopyran-4(4H)-one, characterized by a reactive group adjacent to the C=O function, with the suitable binucleophile amidines in a basic medium. All the new compounds were evaluated for the antiproliferative ability by an in vitro assay on two human tumour cell lines (HL-60 and HeLa), and the 2-phenyl substituted derivative showed the capacity to inhibit cell growth on HL-60. Linear flow dichroism measurements indicated the inability to form a molecular complex with DNA.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
