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

doi:10.1016/j.jorganchem.2016.01.029

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^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

A series of keto-amine bidentate precursors 1–5, OCCH₃CHCCH₃NHR (where 1, R = C₆H₃-2,6-ⁱPr₂; 2, R = C₆H₂-2,4,6-Me₃; 3, R = C₆H₄-2-^tBu; 4, R = C₆H₄-2-OMe; 5, R = C₆H₄-2-OMe-5-Me) were synthesized and combined with [Ru(ɳ⁶-p-cymene)Cl₂]₂ to generate the monomeric arene-Ru derivatives, [Ru(ɳ⁶-p-cymene)(OCCH₃CHCCH₃NR)Cl] (where 6, R = C₆H₃-2,6-ⁱPr₂; 7, R = C₆H₂-2,4,6-Me₃; 8, R = C₆H₄-2-^tBu; 9, R = C₆H₄-2-OMe; 10, R = C₆H₄-2-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 language	English
Pages (from-to)	22-28
Number of pages	7
Journal	Journal of Organometallic Chemistry
Volume	807
DOIs	https://doi.org/10.1016/j.jorganchem.2016.01.029
Publication status	Published - 2016 Apr 1
Externally published	Yes

Keywords

Hormone-refractory prostate cancer
Keto-amine
Ruthenium
Transfer hydrogenation

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.jorganchem.2016.01.029

Cite this

Lin, T. H., Das, K., Datta, A., Leu, W. J., Hsiao, H. C., Lin, C. H., Guh, J. H., & Huang, J. H. (2016). Synthesis and characterization of ruthenium compounds incorporating keto-amine ligands. The applications of catalytic transfer hydrogenation and cancer cell inhibition. Journal of Organometallic Chemistry, 807, 22-28. https://doi.org/10.1016/j.jorganchem.2016.01.029

@article{0e113d876f15480983a5a95d1d175633,

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, OCCH3CHCCH3NHR (where 1, R = C6H3-2,6-iPr2; 2, R = C6H2-2,4,6-Me3; 3, R = C6H4-2-tBu; 4, R = C6H4-2-OMe; 5, R = C6H4-2-OMe-5-Me) were synthesized and combined with [Ru(ɳ6-p-cymene)Cl2]2 to generate the monomeric arene-Ru derivatives, [Ru(ɳ6-p-cymene)(OCCH3CHCCH3NR)Cl] (where 6, R = C6H3-2,6-iPr2; 7, R = C6H2-2,4,6-Me3; 8, R = C6H4-2-tBu; 9, R = C6H4-2-OMe; 10, R = C6H4-2-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.",

keywords = "Hormone-refractory prostate cancer, Keto-amine, Ruthenium, Transfer hydrogenation",

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 Huang, {Jui Hsien}",

note = "Funding Information: The authors express their appreciation to the Ministry of Science and Technology, Taiwan for financial assistance ( NSC 102-2738-M-018-001 ). We also thank the National Changhua University of Education for supporting the facility of X-ray diffractometer and NMR spectrometer. Publisher Copyright: {\textcopyright} 2016 Elsevier B.V.",

year = "2016",

month = apr,

day = "1",

doi = "10.1016/j.jorganchem.2016.01.029",

language = "English",

volume = "807",

pages = "22--28",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier",

}

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

N1 - Funding Information: The authors express their appreciation to the Ministry of Science and Technology, Taiwan for financial assistance ( NSC 102-2738-M-018-001 ). We also thank the National Changhua University of Education for supporting the facility of X-ray diffractometer and NMR spectrometer. Publisher Copyright: © 2016 Elsevier B.V.

PY - 2016/4/1

Y1 - 2016/4/1

N2 - A series of keto-amine bidentate precursors 1–5, OCCH3CHCCH3NHR (where 1, R = C6H3-2,6-iPr2; 2, R = C6H2-2,4,6-Me3; 3, R = C6H4-2-tBu; 4, R = C6H4-2-OMe; 5, R = C6H4-2-OMe-5-Me) were synthesized and combined with [Ru(ɳ6-p-cymene)Cl2]2 to generate the monomeric arene-Ru derivatives, [Ru(ɳ6-p-cymene)(OCCH3CHCCH3NR)Cl] (where 6, R = C6H3-2,6-iPr2; 7, R = C6H2-2,4,6-Me3; 8, R = C6H4-2-tBu; 9, R = C6H4-2-OMe; 10, R = C6H4-2-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, OCCH3CHCCH3NHR (where 1, R = C6H3-2,6-iPr2; 2, R = C6H2-2,4,6-Me3; 3, R = C6H4-2-tBu; 4, R = C6H4-2-OMe; 5, R = C6H4-2-OMe-5-Me) were synthesized and combined with [Ru(ɳ6-p-cymene)Cl2]2 to generate the monomeric arene-Ru derivatives, [Ru(ɳ6-p-cymene)(OCCH3CHCCH3NR)Cl] (where 6, R = C6H3-2,6-iPr2; 7, R = C6H2-2,4,6-Me3; 8, R = C6H4-2-tBu; 9, R = C6H4-2-OMe; 10, R = C6H4-2-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.

KW - Hormone-refractory prostate cancer

KW - Keto-amine

KW - Ruthenium

KW - Transfer hydrogenation

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U2 - 10.1016/j.jorganchem.2016.01.029

DO - 10.1016/j.jorganchem.2016.01.029

M3 - Article

AN - SCOPUS:85029621145

SN - 0022-328X

VL - 807

SP - 22

EP - 28

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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