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^*

^*此作品的通信作者

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

8 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	22-28
頁數	7
期刊	Journal of Organometallic Chemistry
卷	807
DOIs	https://doi.org/10.1016/j.jorganchem.2016.01.029
出版狀態	已發佈 - 2016 4月 1
對外發佈	是

ASJC Scopus subject areas

生物化學
物理與理論化學
有機化學
無機化學
材料化學

UN SDG

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10.1016/j.jorganchem.2016.01.029

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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

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.

於: Journal of Organometallic Chemistry, 卷 807, 01.04.2016, p. 22-28.

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

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. 於: Journal of Organometallic Chemistry. 2016 ; 卷 807. 頁 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, 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",

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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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UR - http://www.scopus.com/inward/citedby.url?scp=85029621145&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2016.01.029

DO - 10.1016/j.jorganchem.2016.01.029

M3 - Article

AN - SCOPUS:85029621145

VL - 807

SP - 22

EP - 28

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

ER -

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

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