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

Autor: Al-Refai M; Department of Chemistry, Faculty of Science, Al al-Bayt University, P.O.BOX 130040, Al-Mafraq 25113, Jordan., Ibrahim MM; Department of Chemistry, Faculty of Science, Al al-Bayt University, P.O.BOX 130040, Al-Mafraq 25113, Jordan., Azmi MN; School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia., Osman H; School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia., Bakar MHA; Bioprocess Technology Division, School of Industrial Technology, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia., Geyer A; Faculty of Chemistry, Philipps University Marburg, Hans-Meerwein-Straße 4, 35032 Marburg, Germany.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2019 Nov 10; Vol. 24 (22). Date of Electronic Publication: 2019 Nov 10.
DOI: 10.3390/molecules24224072
Abstrakt: 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.
Competing Interests: The authors declare no conflict of interest.
Databáze: MEDLINE
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