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

11 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

UN SDGs

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

SDG 3 Good Health and Well-being

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

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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 = "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 BV",

}

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, 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

UR - https://www.scopus.com/pages/publications/85029621145

UR - https://www.scopus.com/pages/publications/85029621145#tab=citedBy

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

UN SDGs

Keywords

ASJC Scopus subject areas

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