Synthesis of novel fluorinated chalcones derived from 4′-morpholinoacetophenone and their antiproliferative effects

Kurşun Aktar B. S., Oruç-Emre E. E., Demirtaş İ., Yaglioglu A. S., Guler C., Adem S., ...More

Journal of Molecular Structure, vol.1149, pp.632-639, 2017 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 1149
  • Publication Date: 2017
  • Doi Number: 10.1016/j.molstruc.2017.08.014
  • Journal Name: Journal of Molecular Structure
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.632-639
  • Keywords: Anticancer activity, Morpholine analogs, PKM 2, Prop-2-en-1-one
  • Ondokuz Mayıs University Affiliated: No

Abstract

The fluorinated chalcones were synthesized by Claisen-Schmidt condensation between 4′-morpholineacetophenone and various fluorinated benzaldehydes in the presence of NaOH in methanol. The synthesized compounds [1–7] were evaluated their antiproliferative activity against HeLa and C6 cell lines. Among them, compounds 4 and 5 were determined to have anticancer activity against HeLa cells line (IC50 values of 7.74 and 6.10 μg/mL, respectively). The anticancer activity results were shown that compounds 3, and 6 had inhibitory against C6 cells (IC50 values of 12.80 and 4.16 μg/mL, respectively). The compounds 1 and 2 had high antiproliferative activity with non-cytotoxicity. All of the new compounds, except for compound 4 showed inhibition against the human isozyme hCA I with IC50 in the range of 0.5–1,16 mM. Pyruvate kinase M2 (PKM2) was effectively inhibited by compound 4 with IC50 = 26 μM.