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Synthesis and in vitro antiproliferative activity of new substituted benzo[3′,2′:5,6]thiopyrano[4,3-d]pyrimidines

✍ Scribed by Anna Maria Marini; Federico Da Settimo; Silvia Salerno; Concettina La Motta; Francesca Simorini; Sabrina Taliani; Daniele Bertini; Ornella Gia; Lisa Dalla Via

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
261 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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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(4__H__)‐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.

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