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

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  • Additional Information
    • Source:
      Publisher: MDPI Country of Publication: Switzerland NLM ID: 100964009 Publication Model: Electronic Cited Medium: Internet ISSN: 1420-3049 (Electronic) Linking ISSN: 14203049 NLM ISO Abbreviation: Molecules Subsets: MEDLINE
    • Publication Information:
      Original Publication: Basel, Switzerland : MDPI, c1995-
    • Subject Terms:
      Chemistry Techniques, Synthetic* ; Structure-Activity Relationship*; Antineoplastic Agents/*chemical synthesis ; Antineoplastic Agents/*pharmacology; Cell Line, Tumor ; Cell Survival/drug effects ; Humans ; Magnetic Resonance Spectroscopy ; Molecular Structure
    • Abstract:
      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.
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    • Contributed Indexing:
      Keywords: breast cancer; carbonitrile; cytotoxicity; liver cancer; malononitrile; methoxypyridine; prostate cancer; thiophene
    • Accession Number:
      0 (Antineoplastic Agents)
    • Publication Date:
      Date Created: 20191114 Date Completed: 20200406 Latest Revision: 20200408
    • Publication Date:
      20240829
    • Accession Number:
      PMC6891325
    • Accession Number:
      10.3390/molecules24224072
    • Accession Number:
      31717690