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MedChemComm | 2011

Platinum-oxazoline complexes as anti-cancer agents: syntheses, characterisation and initial biological studies

Paras N. Yadav; Ramsay E. Beveridge; Jonathan Blay; Alaina R. Boyd; Maja W. Chojnacka; Andreas Decken; Ankur A. Deshpande; Michael G. Gardiner; Trevor W. Hambley; Michael J. Hughes; Leslie Jolly; Jacquelyn A. Lavangie; Timothy D. MacInnis; Sherri A. McFarland; Elizabeth J. New; Robert A. Gossage

The syntheses, characterisation and biological activities (IC50; DNA binding) of four mononuclear Pt oxazoline complexes are reported. These materials are the compounds cis-[PtCl2(NH3)(Etox-κ1N)] (1: Etox = 2-ethyl-2-oxazoline), [PtCl2(anilox-κ2N,N′)] (2: anilox = 4,4-dimethyl-2-[o-anilinyl]-2-oxazoline), cis-[PtCl2(Etox-κ1N)2] (3) and [PtCl(pyox-κ3N,N′,N′)] (4: pyoxH = pyridine-2-carboxyanil-[o-{4,4-dimethyl-2-oxazolinyl}-ide]) and all four are shown to have slightly lower cytotoxicities in vitro when compared to cisplatin against the A2780 ovarian cancer cell line. These new materials all appear to be bio-active via the formation of DNA adducts. Complexes 1 and 2 have been further characterised in the solid-state by X-ray diffraction methods.


Bioorganic & Medicinal Chemistry Letters | 2011

Synthesis and biological activities of 4-N-(anilinyl-n-[oxazolyl])-7-chloroquinolines (n=3' or 4') against Plasmodium falciparum in in vitro models.

Erin E. Gordey; Paras N. Yadav; Marcus P. Merrin; Jill Davies; Steven A. Ward; Grant M.J. Woodman; Amber L. Sadowy; Todd G. Smith; Robert A. Gossage

The synthesis (Pd-mediated coupling strategy) and characterization (NMR, IR, elemental analysis, etc.) of a short series of quinoline-oxazole hybrid compounds has been carried out. These materials are found to be moderately active against Plasmodium falciparum in vitro, with activities in the sub-micromolar range, and to display acceptable cytotoxicity to mononuclear leukocytes. Chemical modification strategies, with the intention to increase the biological potency of this new class of anti-malarial agents, are discussed.


Zeitschrift für Naturforschung B | 2009

An Exploration of the Metal Oxide-assisted Decomposition and Rearrangement of N-Acyl-1,3-oxazolidin-2-ones Leading to 2-Aryl-2-oxazolines [1]

Ankur A. Deshpande; Robert A. Gossagea; Sarah M. Jackson; J. Wilson Quail; Amber L. Sadowy; Paras N. Yadav

An exploration into the utility of the thermally-induced (metal oxide-mediated) CO2 extrusion and subsequent rearrangement of N-acyl-1,3-oxazolidin-2-ones to form 2-aryl(alkyl)-2-oxazolines is described. The reaction is found to give moderate yields of the corresponding 2-oxazolines. Attempts to employ the above methodology to give enantiopure (R)- or (S)-2,5-diphenyl-2-oxazoline (the latter form being the natural product Oxytriphine) from enantiopure (and crystallographically characterised) (S)-N-benzoyl-5-phenyl-2-oxazolidinone led to the isolation of an essentially racemic product. These protocols are compared to other common methods used to form the oxazoline ring system and are placed into context with previous investigations of such ring forming reactions. Graphical Abstract An Exploration of the Metal Oxide-assisted Decomposition and Rearrangement of N-Acyl-1,3-oxazolidin-2-ones Leading to 2-Aryl-2-oxazolines [1]


Tetrahedron Letters | 2004

Application of an air stable Pd oxazoline complex for Heck, Suzuki, Sonogashira and related C-C bond-forming reactions

Robert A. Gossage; Hilary A. Jenkins; Paras N. Yadav


Tetrahedron | 2006

Oxazoline Chemistry. Part 11: Syntheses of natural and synthetic isoflavones, stilbenes and related species via C–C bond formation promoted by a Pd–oxazoline complex

Charles R. Eisnor; Robert A. Gossage; Paras N. Yadav


Canadian Journal of Chemistry | 2005

Oxazoline chemistry. Part VIII. Synthesis and characterization of a new class of pincer ligands derived from the 2-(o-anilinyl)-2-oxazoline skeleton : Applications to the synthesis of group x transition metal catalysts

Andreas Decken; Robert A. Gossage; Paras N. Yadav


Canadian Journal of Chemistry | 2009

Zinc halide oxazoline complexes — The quest for structural diversity

Robert A. Gossage; Paras N. Yadav; Timothy D. MacInnis; J. Wilson Quail; Andreas Decken


Tetrahedron Letters | 2005

Corrigendum to “Application of an air stable Pd oxazoline complex for Heck, Suzuki, Sonogashira and related C–C bond-forming reactions”: [Tetrahedron Lett. 45 (2004) 7689]

Robert A. Gossage; Hilary A. Jenkins; Paras N. Yadav


Acta Crystallographica Section E: Crystallographic Communications | 2006

2-(3-Nitro­phen­yl)-2-oxazoline

Andreas Decken; Laura Botelho; Amber L. Sadowy; Paras N. Yadav; Robert A. Gossage


Analytical Sciences: X-ray Structure Analysis Online | 2008

Crystal Structure of trans-Bis[2-(p-fluorophenyl)-2-oxazoline-κ1N]platinum(II) dichloride]

Paras N. Yadav; Robert A. Gossage; Andreas Decken

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Andreas Decken

University of New Brunswick

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