Ruthenium (II) complexes containing dehydroacetic acid and its imine derivative ligands. Synthesis, characterization and cancer cell growth anti-proliferation activity (GI 50 ) 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

Research output: Contribution to journalArticle

Abstract

Two dehydroacetic acid (DHA, L 1 H) related imine ligands, L 2 H and L 3 H were obtained in moderate yields by reacting DHA with 2,4,6-trimethylaniline and phenylhydrazine, respectively. Refluxing [Ru (η 6 -p-cymene)Cl 2 ] 2 with two equivalents of L 1 Na, L 2 H and L 3 H in methanol generated ruthenium compounds [Ru (η 6 -p-cymene)Cl (L 1 )] (1), [Ru (η 6 -p-cymene)Cl (L 2 )] (2), [Ru (η 6 -p-cymene)Cl (L 3 )] (3), respectively. The chloride atom of 2 and 3 was substituted by ambidentate ligands N 3 , 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 1 H and 13 C 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
Volume871
DOIs
Publication statusPublished - 2018 Sep 15

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Ruthenium compounds
ruthenium compounds
Imines
Ruthenium
Ruthenium Compounds
Cell growth
imines
ruthenium
cancer
Ligands
Derivatives
ligands
acids
Acids
synthesis
Growth
cultured cells
Neoplasms
X ray crystallography
Seats

All Science Journal Classification (ASJC) codes

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

Cite this

Chen, Kuan Hung ; Lin, Tzung Han ; Hsu, Tzu En ; Li, Yong Jie ; Chen, Guan Hao ; Leu, Wohn Jenn ; Guh, Jih Hwa ; Lin, Chia Her ; Huang, Jui-Hsien. / Ruthenium (II) complexes containing dehydroacetic acid and its imine derivative ligands. Synthesis, characterization and cancer cell growth anti-proliferation activity (GI 50 ) study In: Journal of Organometallic Chemistry. 2018 ; Vol. 871. pp. 150-158.
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title = "Ruthenium (II) complexes containing dehydroacetic acid and its imine derivative ligands. Synthesis, characterization and cancer cell growth anti-proliferation activity (GI 50 ) study",
abstract = "Two dehydroacetic acid (DHA, L 1 H) related imine ligands, L 2 H and L 3 H were obtained in moderate yields by reacting DHA with 2,4,6-trimethylaniline and phenylhydrazine, respectively. Refluxing [Ru (η 6 -p-cymene)Cl 2 ] 2 with two equivalents of L 1 Na, L 2 H and L 3 H in methanol generated ruthenium compounds [Ru (η 6 -p-cymene)Cl (L 1 )] (1), [Ru (η 6 -p-cymene)Cl (L 2 )] (2), [Ru (η 6 -p-cymene)Cl (L 3 )] (3), respectively. The chloride atom of 2 and 3 was substituted by ambidentate ligands N 3 , 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 1 H and 13 C 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.",
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Ruthenium (II) complexes containing dehydroacetic acid and its imine derivative ligands. Synthesis, characterization and cancer cell growth anti-proliferation activity (GI 50 ) study . / Chen, Kuan Hung; Lin, Tzung Han; Hsu, Tzu En; Li, Yong Jie; Chen, Guan Hao; Leu, Wohn Jenn; Guh, Jih Hwa; Lin, Chia Her; Huang, Jui-Hsien.

In: Journal of Organometallic Chemistry, Vol. 871, 15.09.2018, p. 150-158.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Ruthenium (II) complexes containing dehydroacetic acid and its imine derivative ligands. Synthesis, characterization and cancer cell growth anti-proliferation activity (GI 50 ) study

AU - Chen, Kuan Hung

AU - Lin, Tzung Han

AU - Hsu, Tzu En

AU - Li, Yong Jie

AU - Chen, Guan Hao

AU - Leu, Wohn Jenn

AU - Guh, Jih Hwa

AU - Lin, Chia Her

AU - Huang, Jui-Hsien

PY - 2018/9/15

Y1 - 2018/9/15

N2 - Two dehydroacetic acid (DHA, L 1 H) related imine ligands, L 2 H and L 3 H were obtained in moderate yields by reacting DHA with 2,4,6-trimethylaniline and phenylhydrazine, respectively. Refluxing [Ru (η 6 -p-cymene)Cl 2 ] 2 with two equivalents of L 1 Na, L 2 H and L 3 H in methanol generated ruthenium compounds [Ru (η 6 -p-cymene)Cl (L 1 )] (1), [Ru (η 6 -p-cymene)Cl (L 2 )] (2), [Ru (η 6 -p-cymene)Cl (L 3 )] (3), respectively. The chloride atom of 2 and 3 was substituted by ambidentate ligands N 3 , 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 1 H and 13 C 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.

AB - Two dehydroacetic acid (DHA, L 1 H) related imine ligands, L 2 H and L 3 H were obtained in moderate yields by reacting DHA with 2,4,6-trimethylaniline and phenylhydrazine, respectively. Refluxing [Ru (η 6 -p-cymene)Cl 2 ] 2 with two equivalents of L 1 Na, L 2 H and L 3 H in methanol generated ruthenium compounds [Ru (η 6 -p-cymene)Cl (L 1 )] (1), [Ru (η 6 -p-cymene)Cl (L 2 )] (2), [Ru (η 6 -p-cymene)Cl (L 3 )] (3), respectively. The chloride atom of 2 and 3 was substituted by ambidentate ligands N 3 , 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 1 H and 13 C 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.

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