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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

1
Department of Chemistry, Faculty of Science, Al al-Bayt University, P.O.BOX 130040, Al-Mafraq 25113, Jordan
2
School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia
3
Bioprocess Technology Division, School of Industrial Technology, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia
4
Faculty of Chemistry, Philipps University Marburg, Hans-Meerwein-Straße 4, 35032 Marburg, Germany
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(22), 4072; https://doi.org/10.3390/molecules24224072 (registering DOI)
Received: 20 October 2019 / Revised: 4 November 2019 / Accepted: 8 November 2019 / Published: 10 November 2019
(This article belongs to the Section Organic Chemistry)
A series of 2-methoxypyridine-3-carbonitrile (5ai)-bearing aryl substituents were successfully synthesized in good yields by the condensation of chalcones (4ai) with malononitrile in basic medium. The condensation process, in most cases, offers a route to a variety of methoxypyridine derivatives (6ag) 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 (IC50 1–5 µM) against those three cancer cell lines.
Keywords: carbonitrile; methoxypyridine; thiophene; malononitrile; cytotoxicity; liver cancer; prostate cancer; breast cancer carbonitrile; methoxypyridine; thiophene; malononitrile; cytotoxicity; liver cancer; prostate cancer; breast cancer
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Al-Refai, M.; Ibrahim, M.M.; Azmi, M.N.; Osman, H.; Bakar, M.H.A.; Geyer, A. The Synthesis, Characterization, Cytotoxic Activity Assessment and Structure–Activity Relationship of 4-Aryl-6-(2,5-dichlorothiophen-3-yl)-2-methoxypyridine-3-carbonitriles. Molecules 2019, 24, 4072.

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