Ruthenium (II) complexes containing dehydroacetic acid and its imine derivative ligands. Synthesis, characterization and cancer cell growth anti-proliferation activity (GI50) study

Kuan Hung Chen, Tzung Han Lin, Tzu En Hsu, Yong Jie Li, Guan Hao Chen, Wohn Jenn Leu, Jih Hwa Guh, Chia Her Lin, Jui Hsien Huang

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Two dehydroacetic acid (DHA, L1H) related imine ligands, L2H and L3H were obtained in moderate yields by reacting DHA with 2,4,6-trimethylaniline and phenylhydrazine, respectively. Refluxing [Ru (η6-p-cymene)Cl2]2 with two equivalents of L1Na, L2H and L3H in methanol generated ruthenium compounds [Ru (η6-p-cymene)Cl (L1)] (1), [Ru (η6-p-cymene)Cl (L2)] (2), [Ru (η6-p-cymene)Cl (L3)] (3), respectively. The chloride atom of 2 and 3 was substituted by ambidentate ligands N3, NCO and NCS to generate a series of ruthenium compounds 4a-4c and 5a-5b. All of these ligands and ruthenium compounds were characterized by 1H and 13C NMR spectroscopy. Compounds 1–3, 4a-4c, and 5a were also structural determined by single crystal X-ray crystallography showing a three-legged piano stool geometry with the p-cymene acting as the seat plane. Anti-proliferative activity study using these ruthenium complexes against PC-3 and DU-145 cell-lines shows that compounds 2 and 4a-4c have the best activity than other ruthenium compounds. The results indicate that the ruthenium p-cymene compounds with large steric hindrance of dehydroacetic acid imine derivative ligands exhibit higher anti-proliferative activity against PC-3 and DU-145 cell-lines.

Original languageEnglish
Pages (from-to)150-158
Number of pages9
JournalJournal of Organometallic Chemistry
Publication statusPublished - 2018 Sep 15


All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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