Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Australian Journal of Chemistry

Australian Journal of Chemistry

Volume 66 Number 11 2013

CH13361Biomedical Applications of Clay

Wojciech Chrzanowski, Sally Yunsun Kim and Ensanya Ali Abou Neel
pp. 1315-1322
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Due to its structural flexibility, small particle size, and chemical composition, clay nanostructure materials are continuously expanding into pharmaceutics including for drug delivery and tissue engineering. The structure of clay allows the intercalation of different biomolecules between the clay layers and then controls their release. While in tissue regeneration clay has proved to be effective to stimulate cell differentiation.

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N,N-Dialkyl-N´-chlorosulfonylchloroformamidines 1 underwent a regioselective reaction with 3-aminopyrazoles 2 to produce pyrazolo[1,5-b][1,2,4,6]thiatriazines 3, representatives of a new ring system. Attempted N-acylation of compounds 3 in pyridine gave only 5-(pyridin-4-yl) derivatives. A similar reaction with pyridazine afforded the corresponding pyridazin-4-yl derivative.

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Sesamol is a potent antioxidative constituent of sesame products. We synthesized a family of biaryl derivatives. The antioxidant activity of the new 6-aryl-substituted sesamols was evaluated against the DPPH radical. A very good correlation between computed bond dissociation energies and experimental EC50(DPPH) values was determined.

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Metal 2-(pyridin-3-yl)-4,6-pyrimidine dicarboxylic acid complexes have different structures, ranging from one- to three-dimensions, which are mainly due to different metal ions and the coordination modes of ppmdc2– ligand. Most importantly, the photoluminescent behaviour of these polymers can be tuned by the configuration of the ppmdc2– ligand.

CH13268Study of New Ferrocene Incorporated N,N′-Disubstituted Thioureas as Potential Antitumour Agents

Bhajan Lal, Amin Badshah, Ataf Ali Altaf, Muhammad Nawaz Tahir, Shafiq Ullah and Fazlul Huq
pp. 1352-1360
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This paper describes the synthesis, structural characterization, cytotoxicity against human ovarian tumour models, and nature of interaction with CT-DNA and pBR322 plasmid DNA of four new ferrocene based N,N′-disubstituted thioureas.

CH13178Stimuli-Responsive Films Based on N-Substituted Polyurethane with Different Alkyl Length

Yanyan Wang, Libin Liu, Congde Qiao and Tianduo Li
pp. 1361-1369
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N-Alkyl-substituted polyurethanes with different alkyl chain lengths were synthesised. The effect of chain length of substituent on substitution degree, thermal properties, crystalline state, and surface morphologies were characterised by 1H NMR spectroscopy, differential scanning calorimetry, X-ray diffraction, and atomic force microscopy. Stimuli-responsive films were realised by solvent and heat treatment, and exhibited a reversible switching in surface wettability with a remarkable change in water contact angle of 21°.

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Five coordination polymers have been hydrothermally synthesised using a flexible 1,1′-(1,4-butanediyl)bis(imidazole) as the main ligand and two S-containing dicarboxylates as the auxiliary ligands. The effects of the central metals and dicarboxylates on the structures of coordination polymers have been investigated.

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In this paper, eight mixed-ligand MII coordination polymer were designed and synthesised under hydrothermal conditions. Structural analysis reveals that bptc influences the MII (M = Co, Ni, Cu, and Zn) ions to form 2D layers, which are further extended via the isomeric bpt connectors, leading to numerous coordination polymers, such as 2D layers (for 13, 5), 3D four-connected nets with a short Schläfli symbol of (64.82) (for 4, 6), and 3D four-connected nets with a short Schläfli symbol of (64.82)(5.63.72)0.5 (for 78).

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Positive halogen donors such as N-iodosuccinimide induce solvolysis of the title dienones as model 4-halogenocyclohexa-2,5-dienones by use of different hydroxylic solvents. The solvolysis in a hydroxylic solvent diluted with MeCN, a polar aprotic solvent, improves efficiency compared with that in the pure hydroxylic solvent. The results are accounted for by assuming that a positive halogen donor electrophilically dehalogenates the dienones generating, via the polar transition states, the 4-oxocyclohexa-2,5-cyclohexadienyl cations.

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Suitably designed charged homopolymers derived from ionic liquids formed spherical nanoparticles in water, and underwent a lower critical solution temperature-type phase change in water. The average radius of the homogeneously dispersed nanoparticles was easily controlled by the temperature.

CH13306Synthesis of Sabina δ-Lactones and Sabina δ-Lactams from (+)-Sabinene

Radoslaw Gnilka and Czeslaw Wawrzeńczyk
pp. 1399-1405
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The synthesis of two δ-lactones and two new δ-lactams from natural sabinene is described. The Baeyer–Villiger oxidation of the sabina ketone and Beckmann rearrangement of the sabina ketone oximes were essential steps to obtain lactones and lactams respectively. An attempt to separate sabina ketone oximes is also described.

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The DNA-binding of [Ru(phen)2(cptcp)]2+ (Ru1) and [Ru(phen)2(btcpc)]2+ (Ru2) was investigated. Results suggest that both complexes bind to DNA by intercalation and Ru1 exhibits more effective DNA cleavage activity than Ru2. Ru1 may act as a dual inhibitor of Topo I/II, whereas Ru2 may only act as a single inhibitor of Topo II.

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A chiral multiple catalysis with two chiral units has been proved effective in the domino Michael–Friedel–Crafts alkylation of β-naphthols with α-bromonitroalkenes. This novel and efficient domino reaction affords chiral 1,2-dihydronaphtho[2,1-b]furans in good to high yields and enantioselectivities (up to 93 % yield, 91 % enantiomeric excess).

CH13269Microwave-Assisted Synthesis of Arene Ruthenium(II) Complex as Apoptosis Inducer of A549 Cells

Qiong Wu, Jian Wu, Wen-Jie Mei, Qi Wang, Zhao Zhang, Xiao-Hui Wu, Fen-Yong Sun, Wei-Li Wu, Yan-Hua Chen, Xiao-Ying Hu and Yun-Yi Tao
pp. 1422-1427
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An arene ruthenium(ii) complex coordinated by phenanthroimidazole derivatives has been synthesised under microwave irradiation with high yield. This complex was able to induce apoptosis of A549 cells by strongly binding to DNA, resulting in DNA damage.

CH13352Matrix Metalloproteinase Biosensor Based on a Porous Silicon Reflector

Fransiska S. H. Krismastuti, Stephanie Pace, Elizabeth Melville, Allison Cowin, Tim R. Dargaville and Nicolas H. Voelcker
pp. 1428-1434
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Matrix metalloproteinases are prognostic biomarkers in chronic wound fluid. We report on a label-free optical biosensor based on porous silicon, which is able to detect matrix metalloproteinases in human wound fluid.

CH13332Simple Metal-catalyst-free Production of Carbon Nanostructures

Thomas K. Ellis, Christian Paras, Matthew R. Hill and John A. Stride
pp. 1435-1439
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Hexachlorobenzene is one of the most persistent organic pollutants known; governed by the Stockholm Convention its transit across international borders is restricted. Efficient remediation strategies for such materials are lacking despite industrial legacy stockpiles. A chemical reduction of hexachlorobenzene using metallic sodium is shown to result in high yields of nanostructured carbon at low temperatures.

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Non-covalent assemblies of maghemite-embedded multiwalled carbon nanotubes (MWCNTs) were synthesised and characterised, and their applicability in PbII removal from aqueous solutions in batches magnetically was evaluated. Maximum removal (~96 %, 24 ppm) was achieved in less than 2 h in a pH range of 6–7.

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Complexation of a simple tripyridyl ligand with various copper(ii) salts yielded a family of metallosupramolecular assemblies. The nature of these species was dependent upon the anion identity, with both discrete architectures and coordination polymers obtained.

CH13354Synthesis of Mg Complexes Supported by Tris-(1-pyrazolyl)phosphine

Amymarie K. Bartholomew, Louise M. Guard, Nilay Hazari and Eddie D. Luzik
pp. 1455-1458
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Poly(pyrazolyl) ligands have found widespread utility in inorganic chemistry. We describe the preparation of two Mg coordination compounds supported by the tris(pyrazolyl)phosphine ligand. These are the first crystallographically characterised complexes supported by this ligand. The structures are compared with complexes supported by the more common tris(pyrazolyl)hydroborate and tris(pyrazolyl)methane ligands.

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Professor Kenneth Seddon OBE, one of AJC’s longest-standing Editors, sadly passed away on 21 January from prostate cancer. Ken was one of the world's best ionic liquids experts. His consistent unwavering support, loyalty and advocacy for AJC over the last 10 years will be sorely missed.