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. 2007 Jul 15;17(14):3872-6.
doi: 10.1016/j.bmcl.2007.05.004. Epub 2007 May 6.

Antiproliferative and apoptosis inducing properties of pyrano[3,2-c]pyridones accessible by a one-step multicomponent synthesis

Igor V Magedov  1 , Madhuri Manpadi, Nikolai M Evdokimov, Eerik M Elias, Elena Rozhkova, Marcia A Ogasawara, Jennifer D Bettale, Nikolai M Przheval'skii, Snezna Rogelj, Alexander Kornienko
Affiliations

Antiproliferative and apoptosis inducing properties of pyrano[3,2-c]pyridones accessible by a one-step multicomponent synthesis

Igor V Magedov et al. Bioorg Med Chem Lett. .

Abstract

4-Arylpyrano-[3,2-c]-pyridones have been prepared by a one-step cyclocondensation of 4-hydroxy-1,6-dimethylpyridin-2(1H)-one with various substituted benzaldehydes and malononitrile. These heterocycles exhibit micromolar and submicromolar antiproliferative activity in HeLa and induce apoptosis in Jurkat cell lines. Structure-activity studies performed on a small library of these compounds show a pronounced cytotoxicity enhancing effect of the bromo substituent at the meta position of the C4 aromatic moiety.

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Figures

Figure 1
Figure 1
Structures of biologically active 2-pyridone-containing compounds.
Figure 2
Figure 2
Structures of the scaffold A, pyranopyridone library B and chromene library C.
Figure 3
Figure 3
Three-component synthesis of pyrano-[3,2-c]-pyridones.
Figure 4
Figure 4
Induction of apoptosis in Jurkat cells treated for 36 h with DMSO control, colchicine (5 μM) and selected pyridone library analogues (5 μM) in flow cytometric annexin-V/propidium iodide assay. Error bars represent data from two experiments.
Figure 5
Figure 5
Jurkat cells after 48 h treatment with DMSO control (A), inactive compound 11 (B) and potent analogue 3 (C).
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