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A series of 2-methoxypyridine-3-carbonitrile ( 5a - i )-bearing aryl substituents were successfully synthesized in good yields by the condensation of chalcones ( 4a - i ) with malononitrile in basic medium. The condensation process, in most cases, offers a route to a variety of methoxypyridine derivatives ( 6a - g ) 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 5d, 5g, 5h and 5i exhibit promising antiproliferative effects (IC 50 1-5 µM) against those three cancer cell lines.

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The Synthesis, Characterization, Cytotoxic Activity Assessment and Structure–Activity Relationship of 4-Aryl-6-(2,5-dichlorothiophen-3-yl)-2-methoxypyridine-3-carbonitriles