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.
2008
Marini, ANNA MARIA; DA SETTIMO PASSETTI, Federico; Salerno, Silvia; LA MOTTA, Concettina; Simorini, Francesca; Taliani, Sabrina; Bertini, D; Gia, O; DALLA VIA, L.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/196927
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