Synthesis and crystallographic characterization of multi-donor N-heterocyclic carbene chelating ligands and their silver complexes: Potential use in pharmaceuticals

Jered C. Garrison; Claire A. Tessier; Wiley J. Youngs

doi:10.1016/j.jorganchem.2005.07.102

Synthesis and crystallographic characterization of multi-donor N-heterocyclic carbene chelating ligands and their silver complexes: Potential use in pharmaceuticals

Jered C. Garrison, Claire A. Tessier, Wiley J. Youngs

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

83 Scopus citations

Abstract

The potential for N-heterocyclic carbenes (NHCs) to be used as novel chelating ligands for bio-inorganic pharmaceuticals is discussed. In this paper, we design, synthesize and characterize two NHC precursors, 6 and 7, that we believe have potential for use as metal chelators for pharmaceuticals. The NHC precursors are composed of imidazolium and pyridine rings that would form mixed donor NHCs upon metallation with medicinally relevant metals. The exploration of the silver chemistry of 6 yielded the dimeric silver NHC complex 8[BPh ₄]₂. The study of the silver chemistry of 7 gave 9[1/3(Ag₄Br₇)] and 10[NO₃]₃. Complex 9[1/3(Ag₄Br₇)] appears to be a silver biscarbene charge balanced by a silver bromide anionic cluster. Complex 10[NO₃] ₃ is a trinuclear silver cluster that is stabilized by NHCs and pyridine rings. Silver NHCs have shown themselves to be excellent transmetallation agents for access to other metal NHC systems. It is envisioned that the silver NHCs 8[BPh₄]₂, 9[1/3(Ag₄Br ₇)] and 10[NO₃]₃ will readily transfer to medicinally relevant metals, such ¹⁰⁵Rh.

Original language	English (US)
Pages (from-to)	6008-6020
Number of pages	13
Journal	Journal of Organometallic Chemistry
Volume	690
Issue number	24-25
DOIs	https://doi.org/10.1016/j.jorganchem.2005.07.102
State	Published - Dec 1 2005
Externally published	Yes

Keywords

Imidazolium salts
Mixed donor ligands
Pharmaceuticals
Silver N-heterocyclic carbenes
Trinuclear silver cluster
X-ray

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.jorganchem.2005.07.102

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Synthesis and crystallographic characterization of multi-donor N-heterocyclic carbene chelating ligands and their silver complexes: Potential use in pharmaceuticals. / Garrison, Jered C.; Tessier, Claire A.; Youngs, Wiley J.
In: Journal of Organometallic Chemistry, Vol. 690, No. 24-25, 01.12.2005, p. 6008-6020.

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

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title = "Synthesis and crystallographic characterization of multi-donor N-heterocyclic carbene chelating ligands and their silver complexes: Potential use in pharmaceuticals",

abstract = "The potential for N-heterocyclic carbenes (NHCs) to be used as novel chelating ligands for bio-inorganic pharmaceuticals is discussed. In this paper, we design, synthesize and characterize two NHC precursors, 6 and 7, that we believe have potential for use as metal chelators for pharmaceuticals. The NHC precursors are composed of imidazolium and pyridine rings that would form mixed donor NHCs upon metallation with medicinally relevant metals. The exploration of the silver chemistry of 6 yielded the dimeric silver NHC complex 8[BPh 4]2. The study of the silver chemistry of 7 gave 9[1/3(Ag4Br7)] and 10[NO3]3. Complex 9[1/3(Ag4Br7)] appears to be a silver biscarbene charge balanced by a silver bromide anionic cluster. Complex 10[NO3] 3 is a trinuclear silver cluster that is stabilized by NHCs and pyridine rings. Silver NHCs have shown themselves to be excellent transmetallation agents for access to other metal NHC systems. It is envisioned that the silver NHCs 8[BPh4]2, 9[1/3(Ag4Br 7)] and 10[NO3]3 will readily transfer to medicinally relevant metals, such 105Rh.",

keywords = "Imidazolium salts, Mixed donor ligands, Pharmaceuticals, Silver N-heterocyclic carbenes, Trinuclear silver cluster, X-ray",

author = "Garrison, {Jered C.} and Tessier, {Claire A.} and Youngs, {Wiley J.}",

note = "Funding Information: This material is based upon work supported by the National Science Foundation under Grant No. 0315980. Acknowledgement is made to the donors of The Petroleum Research Fund, administered by the American Chemical Society, for partial support of this research. We would also like to thank the National Institutes of Health for partial support of this research. ",

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doi = "10.1016/j.jorganchem.2005.07.102",

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T1 - Synthesis and crystallographic characterization of multi-donor N-heterocyclic carbene chelating ligands and their silver complexes

T2 - Potential use in pharmaceuticals

AU - Garrison, Jered C.

AU - Tessier, Claire A.

AU - Youngs, Wiley J.

N1 - Funding Information: This material is based upon work supported by the National Science Foundation under Grant No. 0315980. Acknowledgement is made to the donors of The Petroleum Research Fund, administered by the American Chemical Society, for partial support of this research. We would also like to thank the National Institutes of Health for partial support of this research.

PY - 2005/12/1

Y1 - 2005/12/1

N2 - The potential for N-heterocyclic carbenes (NHCs) to be used as novel chelating ligands for bio-inorganic pharmaceuticals is discussed. In this paper, we design, synthesize and characterize two NHC precursors, 6 and 7, that we believe have potential for use as metal chelators for pharmaceuticals. The NHC precursors are composed of imidazolium and pyridine rings that would form mixed donor NHCs upon metallation with medicinally relevant metals. The exploration of the silver chemistry of 6 yielded the dimeric silver NHC complex 8[BPh 4]2. The study of the silver chemistry of 7 gave 9[1/3(Ag4Br7)] and 10[NO3]3. Complex 9[1/3(Ag4Br7)] appears to be a silver biscarbene charge balanced by a silver bromide anionic cluster. Complex 10[NO3] 3 is a trinuclear silver cluster that is stabilized by NHCs and pyridine rings. Silver NHCs have shown themselves to be excellent transmetallation agents for access to other metal NHC systems. It is envisioned that the silver NHCs 8[BPh4]2, 9[1/3(Ag4Br 7)] and 10[NO3]3 will readily transfer to medicinally relevant metals, such 105Rh.

AB - The potential for N-heterocyclic carbenes (NHCs) to be used as novel chelating ligands for bio-inorganic pharmaceuticals is discussed. In this paper, we design, synthesize and characterize two NHC precursors, 6 and 7, that we believe have potential for use as metal chelators for pharmaceuticals. The NHC precursors are composed of imidazolium and pyridine rings that would form mixed donor NHCs upon metallation with medicinally relevant metals. The exploration of the silver chemistry of 6 yielded the dimeric silver NHC complex 8[BPh 4]2. The study of the silver chemistry of 7 gave 9[1/3(Ag4Br7)] and 10[NO3]3. Complex 9[1/3(Ag4Br7)] appears to be a silver biscarbene charge balanced by a silver bromide anionic cluster. Complex 10[NO3] 3 is a trinuclear silver cluster that is stabilized by NHCs and pyridine rings. Silver NHCs have shown themselves to be excellent transmetallation agents for access to other metal NHC systems. It is envisioned that the silver NHCs 8[BPh4]2, 9[1/3(Ag4Br 7)] and 10[NO3]3 will readily transfer to medicinally relevant metals, such 105Rh.

KW - Imidazolium salts

KW - Mixed donor ligands

KW - Pharmaceuticals

KW - Silver N-heterocyclic carbenes

KW - Trinuclear silver cluster

KW - X-ray

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JF - Journal of Organometallic Chemistry

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ER -

Synthesis and crystallographic characterization of multi-donor N-heterocyclic carbene chelating ligands and their silver complexes: Potential use in pharmaceuticals

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Keywords

ASJC Scopus subject areas

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