Synthesis and evaluation of antitumor activity of some thiazolo[4,5-b]pyridines
Aim. To synthesize a series of novel 3H-thiazolo[4,5-b]pyridine-2-ones by structural modification of the core heterocycle in its N3- and N6-positions and to evaluate their anticancer activity in vitro on several tumor cell lines. Methods. Organic synthesis, 1 H-NMR spectroscopy, trypan blue cell v...
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| Datum: | 2012 |
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| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | English |
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Інститут молекулярної біології і генетики НАН України
2012
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| Schriftenreihe: | Вiopolymers and Cell |
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| Назва журналу: | Digital Library of Periodicals of National Academy of Sciences of Ukraine |
| Zitieren: | Synthesis and evaluation of antitumor activity of some thiazolo[4,5-b]pyridines / T.I. Chaban, R.R. Panchuk, O.V. Klenina, N.R. Skorokhyd, V.V. Ogurtsov, I.G. Chaban // Вiopolymers and Cell. — 2012. — Т. 28, № 5. — С. 389-396. — Бібліогр.: 18 назв. — англ. |
Institution
Digital Library of Periodicals of National Academy of Sciences of Ukraine| Zusammenfassung: | Aim. To synthesize a series of novel 3H-thiazolo[4,5-b]pyridine-2-ones by structural modification of the core heterocycle in its N3- and N6-positions and to evaluate their anticancer activity in vitro on several tumor cell lines.
Methods. Organic synthesis, 1
H-NMR spectroscopy, trypan blue cell viability assay. Results. A new convenient
synthetic approach was developed and optimized conditions were studied for the reaction of preparation of 3Hthiazolo[4,5-b]pyridin-2-one derivatives. 5,7-Dimethyl-3H-thiazolo[4,5-b]pyridin-2-one and 6-phenylazo-5,7-
dimethyl-3H-thiazolo[4,5-b]pyridin-2-one were obtained by [3 + 3]cyclocondensation of 4-iminothiazolidone2 with acetylacetone and -phenylazoacetylacetone in methanol medium in the presence of sodium methylate.
They were used as starting compounds for further structural modification of the core thiazolo[4,5-b]pyridine heterocycle in its 3- and 6-positions. On the basis of in vitro cytotoxicity studies of synthesized compounds several
structure-functional relationships underlying anticancer potential of 5,7-dimethyl-3H-thiazolo[4,5-b]pyridin2-one derivatives were identified. Conclusions. 3H-thiazolo[4,5-b]pyridin-2-one can be considered as a promising molecular scaffold for rational design of potential anticancer drug candidates. Introduction of phenylazo
substitute at C6-position of 3H-thiazolo[4,5-b]pyridin-2-one proved to be the most efficient, as it led to 3-fold increase of its anticancer potential.
Keywords: thiazolo[4,5-b]pyridines, [3+ 3]cyclocondensation, structural modification, antitumor activity |
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