Synthesis and antiproliferative evaluation of some new amidino-substituted bis-benzothiazolyl-pyridines and pyrazine (CROSBI ID 185040)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Racané, Livio ; Kraljević Pavelić, Sandra ; Ratkaj, Ivana ; Stepanić, Višnja ; Pavelić, Krešimir ; Tralić-Kulenovića, Vesna ; Karminski-Zamola, Grace
engleski
Synthesis and antiproliferative evaluation of some new amidino-substituted bis-benzothiazolyl-pyridines and pyrazine
Novel diamidino substituted conformationally restricted derivatives of bis-benzothiazolyl-pyridines and pyrazine were synthesized and their antiproliferative activity against several human cancer cell lines were determinated. The synthetic approach used for preparation of isomeric amidinobenzotiazolyl disubstituted pyridines 3a-3k and pyrazine 3l was achieved by condenzation reaction of commercially available pyridine and pyrazine dicarboxylic acids with amidino- 2a and 2-imidazolinyl-substituted 2-aminothiophenol 2b in polyphosphoric acid in moderate to good yield. The condenzation reaction was greatly optimized. The targeted compounds were converted in the desired water soluble dihydrochloride salts by reaction of appropriate free base with concd HCl in ethanol or acetic acid. Antiproliferative assays revealed significant differences in antiproliferative activities of diamidino– and diimidazolinyl- derivatives, the latter exerting stronger concentration-dependent antiproliferative effects on tested tumor cell lines and thus being a prominent compound class for further chemical optimization and biological studies. Biological studies on SW620 cell line and BJ fibroblasts perfomed for the diimidazolinyl- derivative 3b revealed oxidative stress as a possible mechanism of antiproliferative action and predicted antineoplastic properties for this class of compounds.
synthesis ; bis-benzothiazolyl substituted pyridines and pyrazine ; amidines ; antiproliferative activity
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Podaci o izdanju
55
2012.
108-116
objavljeno
0223-5234
1768-3254
10.1016/j.ejmech.2012.07.005
Povezanost rada
Kemija, Biologija