Synthesis and characterization of ruthenium compounds incorporating keto-amine ligands. The applications of catalytic transfer hydrogenation and cancer cell inhibition

Tzung Han Lin, Kuheli Das, Amitabha Datta, Wohn Jenn Leu, Hung Chang Hsiao, Chia Her Lin, Jih Hwa Guh, Jui-Hsien Huang

Research output: Contribution to journalArticle

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Abstract

A series of keto-amine bidentate precursors 1–5, OCCH 3 CHCCH 3 NHR (where 1, R = C 6 H 3 -2,6- i Pr 2 ; 2, R = C 6 H 2 -2,4,6-Me 3 ; 3, R = C 6 H 4 -2- t Bu; 4, R = C 6 H 4 -2-OMe; 5, R = C 6 H 4 -2-OMe-5-Me) were synthesized and combined with [Ru(ɳ 6 -p-cymene)Cl 2 ] 2 to generate the monomeric arene-Ru derivatives, [Ru(ɳ 6 -p-cymene)(OCCH 3 CHCCH 3 NR)Cl] (where 6, R = C 6 H 3 -2,6- i Pr 2 ; 7, R = C 6 H 2 -2,4,6-Me 3 ; 8, R = C 6 H 4 -2- t Bu; 9, R = C 6 H 4 -2-OMe; 10, R = C 6 H 4 -2-OMe-5-Me) in moderate yield. The ruthenium derivatives effectively catalyzed the conversion rate in transfer hydrogenation of substituted acetophenone. The molecular structures of 2, 6–10 were determined by single crystal X-ray diffractometry in the solid state, revealing a four-coordination environment around the Ru atom. The potential anti-cancer activity of ruthenium derivatives against human hormone-refractory metastatic prostate cancer (HRMPC) cell lines was also studied.

Original languageEnglish
Pages (from-to)22-28
Number of pages7
JournalJournal of Organometallic Chemistry
Volume807
DOIs
Publication statusPublished - 2016 Apr 1

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Ruthenium Compounds
Ruthenium compounds
ruthenium compounds
Hydrogenation
Ruthenium
ruthenium
hydrogenation
Amines
amines
cancer
Ligands
Cells
Derivatives
ligands
hormones
refractories
synthesis
Molecular Structure
cultured cells
Neoplasms

All Science Journal Classification (ASJC) codes

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

Cite this

Lin, Tzung Han ; Das, Kuheli ; Datta, Amitabha ; Leu, Wohn Jenn ; Hsiao, Hung Chang ; Lin, Chia Her ; Guh, Jih Hwa ; Huang, Jui-Hsien. / Synthesis and characterization of ruthenium compounds incorporating keto-amine ligands. The applications of catalytic transfer hydrogenation and cancer cell inhibition. In: Journal of Organometallic Chemistry. 2016 ; Vol. 807. pp. 22-28.
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title = "Synthesis and characterization of ruthenium compounds incorporating keto-amine ligands. The applications of catalytic transfer hydrogenation and cancer cell inhibition",
abstract = "A series of keto-amine bidentate precursors 1–5, OCCH 3 CHCCH 3 NHR (where 1, R = C 6 H 3 -2,6- i Pr 2 ; 2, R = C 6 H 2 -2,4,6-Me 3 ; 3, R = C 6 H 4 -2- t Bu; 4, R = C 6 H 4 -2-OMe; 5, R = C 6 H 4 -2-OMe-5-Me) were synthesized and combined with [Ru(ɳ 6 -p-cymene)Cl 2 ] 2 to generate the monomeric arene-Ru derivatives, [Ru(ɳ 6 -p-cymene)(OCCH 3 CHCCH 3 NR)Cl] (where 6, R = C 6 H 3 -2,6- i Pr 2 ; 7, R = C 6 H 2 -2,4,6-Me 3 ; 8, R = C 6 H 4 -2- t Bu; 9, R = C 6 H 4 -2-OMe; 10, R = C 6 H 4 -2-OMe-5-Me) in moderate yield. The ruthenium derivatives effectively catalyzed the conversion rate in transfer hydrogenation of substituted acetophenone. The molecular structures of 2, 6–10 were determined by single crystal X-ray diffractometry in the solid state, revealing a four-coordination environment around the Ru atom. The potential anti-cancer activity of ruthenium derivatives against human hormone-refractory metastatic prostate cancer (HRMPC) cell lines was also studied.",
author = "Lin, {Tzung Han} and Kuheli Das and Amitabha Datta and Leu, {Wohn Jenn} and Hsiao, {Hung Chang} and Lin, {Chia Her} and Guh, {Jih Hwa} and Jui-Hsien Huang",
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Synthesis and characterization of ruthenium compounds incorporating keto-amine ligands. The applications of catalytic transfer hydrogenation and cancer cell inhibition. / Lin, Tzung Han; Das, Kuheli; Datta, Amitabha; Leu, Wohn Jenn; Hsiao, Hung Chang; Lin, Chia Her; Guh, Jih Hwa; Huang, Jui-Hsien.

In: Journal of Organometallic Chemistry, Vol. 807, 01.04.2016, p. 22-28.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and characterization of ruthenium compounds incorporating keto-amine ligands. The applications of catalytic transfer hydrogenation and cancer cell inhibition

AU - Lin, Tzung Han

AU - Das, Kuheli

AU - Datta, Amitabha

AU - Leu, Wohn Jenn

AU - Hsiao, Hung Chang

AU - Lin, Chia Her

AU - Guh, Jih Hwa

AU - Huang, Jui-Hsien

PY - 2016/4/1

Y1 - 2016/4/1

N2 - A series of keto-amine bidentate precursors 1–5, OCCH 3 CHCCH 3 NHR (where 1, R = C 6 H 3 -2,6- i Pr 2 ; 2, R = C 6 H 2 -2,4,6-Me 3 ; 3, R = C 6 H 4 -2- t Bu; 4, R = C 6 H 4 -2-OMe; 5, R = C 6 H 4 -2-OMe-5-Me) were synthesized and combined with [Ru(ɳ 6 -p-cymene)Cl 2 ] 2 to generate the monomeric arene-Ru derivatives, [Ru(ɳ 6 -p-cymene)(OCCH 3 CHCCH 3 NR)Cl] (where 6, R = C 6 H 3 -2,6- i Pr 2 ; 7, R = C 6 H 2 -2,4,6-Me 3 ; 8, R = C 6 H 4 -2- t Bu; 9, R = C 6 H 4 -2-OMe; 10, R = C 6 H 4 -2-OMe-5-Me) in moderate yield. The ruthenium derivatives effectively catalyzed the conversion rate in transfer hydrogenation of substituted acetophenone. The molecular structures of 2, 6–10 were determined by single crystal X-ray diffractometry in the solid state, revealing a four-coordination environment around the Ru atom. The potential anti-cancer activity of ruthenium derivatives against human hormone-refractory metastatic prostate cancer (HRMPC) cell lines was also studied.

AB - A series of keto-amine bidentate precursors 1–5, OCCH 3 CHCCH 3 NHR (where 1, R = C 6 H 3 -2,6- i Pr 2 ; 2, R = C 6 H 2 -2,4,6-Me 3 ; 3, R = C 6 H 4 -2- t Bu; 4, R = C 6 H 4 -2-OMe; 5, R = C 6 H 4 -2-OMe-5-Me) were synthesized and combined with [Ru(ɳ 6 -p-cymene)Cl 2 ] 2 to generate the monomeric arene-Ru derivatives, [Ru(ɳ 6 -p-cymene)(OCCH 3 CHCCH 3 NR)Cl] (where 6, R = C 6 H 3 -2,6- i Pr 2 ; 7, R = C 6 H 2 -2,4,6-Me 3 ; 8, R = C 6 H 4 -2- t Bu; 9, R = C 6 H 4 -2-OMe; 10, R = C 6 H 4 -2-OMe-5-Me) in moderate yield. The ruthenium derivatives effectively catalyzed the conversion rate in transfer hydrogenation of substituted acetophenone. The molecular structures of 2, 6–10 were determined by single crystal X-ray diffractometry in the solid state, revealing a four-coordination environment around the Ru atom. The potential anti-cancer activity of ruthenium derivatives against human hormone-refractory metastatic prostate cancer (HRMPC) cell lines was also studied.

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