Synthesis of novel 1,4‐dihydropyrido[3′,2′:5,6]thiopyrano[4,3‐ c ]‐pyrazoles and 5 H ‐pyrido[3′,2′:5,6]thiopyrano[4,3‐ d ]pyrimidines as potential antiproliferative agents

• Published in: Journal of heterocyclic chemistry 2003-09, Vol.40 (5), p.783-788
• Main Authors: Primofiore, Giampaolo, Marini, Anna Maria, Da Settimo, Federico, Salerno, Silvia, Bertini, Daniele, Dalla Via, Lisa, Magno, Sebastiano Marciani
• Format: Article
• Language: English
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.5570400506

The synthesis of new planar derivatives characterized by the presence of a pyridothiopyranopyrazole or pyridothiopyranopyrimidine nucleus, carrying a substituted aryl group, is reported. The novel 1,4‐dihydropyrido[3′,2′:5,6]thiopyrano[4,3‐ c ]pyrazole derivatives were obtained by condensation of 2,3‐dihydro‐3‐hydroxymethylenethiopyrano[2,3‐ b ]pyridin‐4(4 H )‐ones with appropriate hydrazines. The preparation of 2‐substituted pyrido[3′,2′:5,6]thiopyrano[4,3‐ d ]pyrimidines was accomplished from the intermediate 2,3‐dihy‐dro‐3‐dimethylaminomethylenethiopyrano[2,3‐ b ]pyridin‐4(4 H )‐ones by reaction with the appropriate binucleophile amidines. The antiproliferative activity of some new products was tested by an in vitro assay on human tumour cell lines (HL‐60 and HeLa), but none of them showed any significant effects in the tests performed. Accordingly, linear flow dichroism measurements indicated their inability to form a molecular complex with DNA.