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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
Author(s) -
Primofiore Giampaolo,
Marini Anna Maria,
Da Settimo Federico,
Salerno Silvia,
Bertini Daniele,
Dalla Via Lisa,
Magno Sebastiano Marciani
Publication year - 2003
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570400506
Subject(s) - chemistry , hela , stereochemistry , in vitro , biochemistry
Abstract 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.