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A series of 2-methoxypyridine-3-carbonitrile (<b>5a</b>&#8722;<b>i</b>)-bearing aryl substituents were successfully synthesized in good yields by the condensation of chalcones (<b>4a</b>&#8722;<b>i</b>)<b> </b>with malononitrile in basic medium. The condensation process, in most cases, offers a route to a variety of methoxypyridine derivatives (<b>6a</b>&#8722;<b>g</b>) as side products in poor yields. All new compounds were fully characterized using different spectroscopic methods. Mass ESI-HMRS measurements were also performed. Furthermore, these compounds were screened for their in vitro cytotoxicity activities against three cancer cell lines; namely, those of the liver (line HepG2), prostate (line DU145) and breast (line MBA-MB-231). The cytotoxicity assessment revealed that compounds <b>5d, 5g, 5h</b> and <b>5i</b> exhibit promising antiproliferative effects (IC₅₀ 1&#8722;5 &#181;M) against those three cancer cell lines.