Australian Journal of Chemistry
Volume 70 Number 2 2017
Australasian Peptide Chemistry
This special issue of the Journal contains a selection of papers which showcase the cutting edge research being conducted in peptide chemistry today.
As demonstrated in the recent literature, β-peptides can self-assemble into a range of materials. This highlight explores recent developments in the preparation of functional materials involving β-peptides, wherein the self-assembly of β-peptides is unperturbed by side chain functionalisation and leads to the formation of stable gels and scaffolds that can support cellular growth.
CH16425Atomic Force Microscopy Studies of the Interaction of Antimicrobial Peptides with Bacterial Cells
Many antimicrobial peptides (AMPs) are membrane-active but their mode of action remains elusive. Most studies have been conducted with synthetic membrane systems but, more recently, atomic force microscopy has been utilized to reveal the effect of AMPs on bacterial cells and provide great insight into how this class of peptides lyse cells.
CH16532Macrocyclic Peptidomimetics Prepared by Ring-Closing Metathesis and Azide–Alkyne Cycloaddition
Ring-closing metathesis (RCM) and copper(i)-catalyzed azide–alkyne cycloaddition (CuAAC) are powerful strategies to introducing a macrocycle. This review focusses on the current synthetic approaches to access biologically active macrocycles that target important therapeutic aims for conditions such as cancer, cataracts, HIV, and neurological diseases.
Cyclotides are a group of cysteine-rich peptides derived from plants. Their exceptional stability based on their head-to-tail cyclized backbone and cystine knot, together with their tolerance to sequence modifications, make them promising drug design scaffolds into which novel bioactive sequences may be grafted. These grafting applications are achievable by solid-phase peptide synthesis. This article describes recent developments in the chemical synthesis and enzyme-mediated cyclization of cyclotides.
CH16407Synthesis of Multivalent [Lys8]-Oxytocin Dendrimers that Inhibit Visceral Nociceptive Responses
We demonstrate efficient ‘click’ synthesis of large dendrimeric oxidatively folded peptides with up to 16 copies of [Lys8]-oxytocin that maintain potency and structure.
CH16499An Efficient Chemical Synthesis of Lassomycin Enabled by an On-Resin Lactamisation–Off-Resin Methanolysis Strategy and Preparation of Chemical Variants
Lasso peptides contain a unique 3-D topography (known as a lariat knot) and are touted as novel scaffolds for biomedical applications. The synthesis of the non-threaded lasso peptide lassomycin was accomplished by solid-phase peptide chemistry and a novel way to install the C-terminal ester on the fully unprotected peptide.
A stepwise conjugation technique was employed to synthesise a multiantigenic vaccine candidate against Group A streptococcus (GAS) through azide–alkyne cycloaddition and mercapto–maleimide reactions. The final vaccine candidate consists of four different components: two GAS antigens, a T-helper epitope, and the lipidic moiety dipalmitoyl serine (DPS).
CH16510Molecular Insights into the Interaction Between the SPRY Domain-Containing SOCS Box Protein SPSB2 and Peptides Based on the Binding Motif from iNOS
Surface plasmon resonance and NMR spectroscopy were used to gain insights into the binding of iNOS-derived peptides to SPSB2. The complex interplay of peptide sequence and protein binding will inform efforts to design peptide therapeutics to disrupt the iNOS–SPSB interaction.
The introduction of an iterative ‘click’ step into solid phase peptide synthesis protocols provides a method for rapid functionalisation of peptide side chains with a range of diverse moieties.
The fruit fly insulin-like peptide 2, DILP2, is one of seven closely related peptides that each act upon the same insulin-like receptor. It was successfully chemically assembled by regioselective disulfide bond formation within its two synthetic chains and shown to potently stimulate receptor phosphorylation and downstream signalling.
The simple cyclic tetrapeptide cyclo-(1,4)-[Ala-Arg-Ala-homoGlu]-NH2 (3) is shown to adopt an unusual α-turn structure. The latter structure is not α-helical but can nucleate α-helicity when attached to the N-terminus of either model peptides or two biologically relevant peptides. This new N-terminal helix-capping macrocycle provides simple and rapid synthetic access to α-helical peptide structures.
The emergence of antibiotic-resistant microbes and the lack of new antibiotics require development of new antimicrobial molecules and screening assays for them. We provide a proof of concept that a large unilamellar vesicle method used to study chloride ion efflux can be adapted to identify membrane-active antimicrobial peptides and screen their relative activity.
Fijimycin A is a cyclic depsipeptide that has been shown to possess activity against a range of pathogenic bacteria. This communication describes the total synthesis of norfijimycin A, a simplified analogue of the marine natural product fijimycin A. The natural product analogue was shown to possess significant activity against Mycobacterium tuberculosis, the etiological agent of tuberculosis.
The peer-reviewed and edited version of record published online before inclusion in an issue
The HERON reaction, named at the Second Heron Island Conference on Reactive Intermediates and Unusual Molecules, is a modern ‘named reaction’. HERON is an acronym for Heteroatom Rearrangements on Nitrogen, a unique chemical transformation.
CH16716New Heterodinuclear Zn/Ln (Ln = Gd, Tb, Er, Yb) Complexes of Hexadentate N,N′-Bis(3-alkoxy-2-hydroxybenzyl)cyclohexane-1,2-diamines: Synthesis and Structure
N,N′-Bis(3-alkoxy-2-hydroxybenzyl)cyclohexane-1.2-diamines (alkoxy = OCH3, OC2H5) form, with zinc acetate and lanthanide nitrate (Ln = Gd, Tb, Er, Yb) in methanol, the isostructural heterodinuclear complexes [Zn(L)(µ-CH3COO)Ln(NO3)2]. In these complexes, zinc(ii) is coordinated by an N2O3 donor set with trigonal bipyramidal geometry, whereas the lanthanides possess an O9 coordination environment in a capped square antiprismatic configuration.
CH16496DNA Photocleavage and Binding Modes of Methylene Violet 3RAX and its Derivatives: Effect of Functional Groups
Methylene violet 3RAX 1 and its derivatives 2–5 were synthesised and characterised. The binding mode between the synthesised compounds and DNA and their DNA photocleavage ability were investigated. The results suggest that the binding mode between methylene violet 3RAX and DNA, its ability to generate singlet oxygen, and DNA photocleavage activity could be changed through modification of the amino group on methylene violet 3RAX.
CH16682Synthesis of Cross-Linked Poly(acrylamide) Microspheres by Dispersion Polymerisation in Aqueous Ammonium Sulfate Solution
Cross-linked poly(acrylamide) microspheres, PAMBA, with mean diameters ranging from 169.7 to 525.2 nm were successfully prepared by dispersion polymerisation of acrylamide in an aqueous ammonium sulfate solution with N,N′-methylenebis(acrylamide) as the cross-linking agent and sodium dodecyl sulfate as the stabiliser. The mean diameter of the PAMBA microspheres can be controlled by adjusting the concentration of the stabiliser.
CH16600Luminescent Functionalised Supramolecular Coordination Polymers Based on an Aromatic Carboxylic Acid Ligand for Sensing Hg2+ Ions
Two luminescent functionalised supramolecular coordination polymers based on an aromatic carboxylic acid ligand exhibit efficient luminescence sensing for Hg2+ ions.
CH16656A Novel, Interpenetrating Metal–Organic Framework: Synthesis, Structure, and Luminescence Detection of Nitrobenzene
A 3D heterometal–organic framework was synthesised. The compound is 2-fold interpenetrating. It displayed good thermal and solvents stability and exhibited high sensitive and qualitative luminescent detection of nitrobenzene. The present study is the first report on the use of an interpenetrating heterometallic metal–organic framework as a luminescent probe for nitrobenzene
CH16710Synthesis of Two 2,2′-Bipyridine Containing Macrocycles for the Preparation of Interlocked Architectures
The synthesis and characterisation of two 28-membered, 2,2′-bipyridine-containing macrocycles is reported.
CH16673Co-Crystallisation of 1,4-Diiodotetrafluorobenzene with Three Different Symmetric Dipyridylacetylacetone Isomers Produces Four Halogen-Bonded Architectures
The co-crystallisation of the linear halogen-bond donor 1,4-DITFB with three symmetric dipyridylacetylacetone isomers produces four different halogen-bonded networks.
The recovery of platinum from acidic solutions was examined and consists of two steps. For each reaction within a step, the rate constants were determined. The first two reactions in step 1 were diffusion controlled unlike the third reaction in step 2 step, which took place at the surface of activated carbon. The results were in excellent agreement to the assumed model.
The current study presents various CoII bispidine complexes, including a complex with L1 that reacts with dioxygen to produce a CoIII product with the N3-monodeprotonated tetradentate bispidine fragment and a coordinated picolinate originating from L1.
Lanthanide phosphate nanoparticles were produced under continuous flow in a vortex fluidic device in the presence of polyvinylpyrrolidone. Changes in the morphology of the dandelion-shaped nanoparticles were possible by varying the chain length of PVP, and the rotational speed and tilt angle of the tube in the vortex fluidic device.
The transition metal complexes of picolylcyanoacetamides with thiocyanate are presented. Discrete tetrahedral, octahedral, and polymeric structures were isolated, and for cobalt(ii) complexes the magnetic susceptibility was measured.
CH16660A Theoretical Probe for Structures, Metal–Metal Bonding, and Electronic Spectra of Paramagnetic Tetrapyrrolic RuII Complex
The Ru2 double bond in (RuPz)2, composed of one σ bond and one π bond, is unravelled by DFT (B3LYP) and WFT (CASSCF and NEVPT2) calculations. The ground state shows a Ru–Ru distance of 2.38 Å, a stretching frequency of 202 cm-1, and a bonding energy of 30.7 kcal mol-1. This agrees with experimental results.
CH16643Investigation of Selective Microwave Heating Phenomena in the Reactions of 2-Substituted Pyridines
Simultaneous temperature measurement by external and internal sensors revealed hidden inhomogeneities within the reaction mixtures of a debated microwave-assisted benzylation involving a 2-substituted pyridine reagent. Rate enhancement could be explained by macroscopic-scale localized heating in the boundary layers close to the vessel surface.
CH16678Syntheses and Structure Investigations of 3d Transition Metal Complexes with a Flexible N4O2-Donor Hexadentate Schiff-Base Ligand
The syntheses and structure investigations of four new 3d transition metal complexes with a flexible N4O2-donor hexadentate Schiff-base ligand are described. The molecular structures of the FeIII, CoIII, and NiII mononuclear complexes demonstrate distorted octahedral coordination geometry. The CuII complex shows a trinuclear structure.
An environmentally benign and mild method for the in situ formation of NO+ from readily available nitrate salts by treatment with formic acid and MeOH is described. The synthetic applicability of the method was demonstrated for the oxidative phenol–arene C–C cross-coupling by direct C–H activation.
CH16639Salicylaldehyde Hydrazones: Buttressing of Outer-Sphere Hydrogen-Bonding and Copper Extraction Properties
Electron-withdrawing or hydrogen-bond accepting groups increase the strength of salicylaldehyde hydrazone Cu extractants by three orders of magnitude.
CH16555In Situ Spectroelectrochemical Investigations of RuII Complexes with Bispyrazolyl Methane Triarylamine Ligands
Two new triarylamine-based ligands containing the bispyrazolylmethane moiety and their RuII terpyridine complexes exhibit interesting electrochemical and spectroscopic properties. In particular, formation of the triarylamine radical cation leads to an electrochemically induced dimerization process.
The chemical mutability of metal–organic frameworks (MOFs) is an advantageous feature that allows fine-tuning of their physical and chemical properties. Herein, we report the successful isoreticulation of a MOF by modifying the steric bulk and length of the original ligand separately and in combination.
CH16566N-Heterocyclic Carbene-Catalysed Mukaiyama–Michael Reaction and Mukaiyama Aldol/Mukaiyama–Michael Three-Component Coupling Reaction
An N-heterocyclic carbene catalysed Mukaiyama–Michael addition between several TMS enol ethers and chalcone derivatives has been discovered. Also the related dehydrative Mukaiyama aldol followed by a Mukaiyama–Michael addition process has been developed. The enantioselective variant of these reactions has been examined with homochiral catalysts, which are active but fail to achieve enantioinduction.
CH16620Rage Against Conformity: Ruthenium(ɪɪ) Bisterpyridine Complexes Respond to Crystal Engineering Instructions with Whelming Results
Functionalised ruthenium(ii) bisterpyridine complexes refuse to obey crystal-engineering hydrogen-bond instructions.
CH16609Study on the Acid-Induced Ring-Expansion of an Oxaphosphirane Complex with an Electron-Withdrawing C-Substituent
A study on the acid-induced ring-expansion reaction of the first oxaphosphirane complex bearing C6F5 as an electron-withdrawing C-substituent using trifluoromethanesulfonic acid and electronically different aldehydes is described. The stereoselectively obtained 1,3,4-dioxaphospholane complexes 4a–c were unambiguously characterized by elemental analysis, multinuclear NMR, mass spectrometry, and single crystal X-ray diffraction studies.
Nickel–iron hydrogenases produce and consume hydrogen using elaborate electron and proton transport machinery. Although synthetic modelling of nickel–iron hydrogenases has developed rapidly, it has largely ignored aspects of substrate transfer. Reported here are nickel–iron mimics bearing redox-active ferrocenyl ligands, these trinuclear systems representing advanced models of the native enyzmes.
Racemic 4 melts above 350°C despite its low molar mass and absence of Pauling hydrogen bonding. X-Ray and Hirshfeld surface analyses reveal excellent complementarity between homochiral molecules of 4, and layers of opposite handedness are linked by the aza-1,3-peri hydrogen interaction. Weak intermolecular forces are discussed in context of the Lipinski ‘rule of 5’ solubility criteria.
CH16540Synthesis and Liquid Crystalline Properties of a New Homologous Series of 4,5-Disubstituted 2H-[1,2,3]-Triazoles via Azide-Chalcone Oxidative Cycloaddition Reaction
Homologous series of 4,5-disubstituted 2H-[1,2,3]-triazole derivatives were synthesized from chalcones and sodium azide via CuI-catalyzed oxidative cycloaddition reaction in order to characterize their liquid crystalline properties by polarizing optical microscopy and differential scanning calorimetry.
Arguably the most famous of all small molecule reactive intermediates is the hydroxyl radical. Methods to generate hydroxyl radicals from organic precursors are rare, with only one known example for the solution phase. Mass spectrometry is a key identifying technique is this area, and reported herein are new HO and DO radical precursors based on the trimethylammonium benzyl alcohol motif.
Is formate an energy source? We achieve formate electrooxidation in a practical and convenient way. The precursor of the oxidation is free HCOO– in fuel liquid rather than Pt-HCOOH. Formate is able to bypass the undesirable poisoning path to alternatively form carbon dioxide.
CH16543Polyanhydride Nanoparticles: Thiol–Ene ‘Click’ Polymerizations Provide Functionalized and Cross-Linkable Nanoparticles with Tuneable Degradation Times
Degradable polyanhydride-based nanoparticles are synthesized using thiol–ene ‘click’ polymerization followed by emulsification and solvent evaporation. These nanoparticles have tuneable degradation times, can be easily functionalized, and encapsulate payloads that can then be released upon degradation. Such degradable polymer nanoparticles have potential in many nano/bio-theranostic applications.
CH16580Brønsted Base-Mediated Aziridination of 2-Alkyl-Substituted-1,3-Dicarbonyl Compounds and 2-Acyl-Substituted-1,4-Dicarbonyl Compounds by Iminoiodanes
A Brønsted base-mediated method for the synthesis of α,α-diacylaziridines and α,α,β-triacylaziridines from reaction of 2-alkyl-substituted-1,3-dicarbonyl compounds and 2-acyl-substituted-1,4-dicarbonyl compounds with arylsulfonyliminoiodinanes (ArSO2N=IPh) under atmospheric conditions is described.
CH16587Syntheses, Structural Studies, and Copper Iodide Complexes of Macrocycles Derived from Williamson Ether Syntheses Involving 2,9-Bis(4-hydroxyphenyl)-1,10-phenanthroline, α,ω-Dibromides, and Resorcinol or 2,7-Dihydroxynaphthalene
The title macrocycles were assembled by first combining the grey and maroon building blocks, followed by a condensation with 1. The CuI moieties were markedly removed from the 1,10-phenanthroline planes, as represented by the basketball above the basket rim, and voids in the crystals were analyzed in the context of rotaxane formation.
The proton conductivity of graphene oxide has been reduced by 25 % after three years of aging due to the decrease in oxygen content and interlayer distance.
CH16621Interaction of Triplet Excited States of Ketones with Nucleophilic Groups: (π,π*) and (n,π*) versus (σ*,π*) States. Substituent-Induced State Switching in Triplet Ketones
The presence of nucleophilic substituents neighbouring a ketone functional group switches the character of the lowest triplet excited states from (π,π*) or (n,π*) to (σ*,π*).
CH16455Ilimaquinone and 5-epi-Ilimaquinone: Beyond a Simple Diastereomeric Ratio, Biosynthetic Considerations from NMR-Based Analysis
Ilimaquinone is a biologically active sesquiterpene isolated from Dactylospongia sponges. An intriguing diastereomeric ratio is observed based on an impressive collection of samples. Biosynthetic and ecological considerations stem from this study.
Two Q-based supramolecular assemblies were prepared via different approaches, and these Q-based supramolecular assemblies possess porous features that suggest that Q[n]-based compounds could be used to manufacture molecular sieves and sensors and applied in absorption and separation technologies
CH16556Molecular Assemblies and Spin-Crossover Behaviour of Cobalt(ɪɪ) Complexes with Terpyridine Incorporating Different Nitrogen Positions in Pyridine Rings
Cobalt(ii) complexes with terpyridine-type ligands, [Co(n-pyterpy)2](ClO4)2 (n = 3 (1), 4 (2)), show different molecular assemblies depending on the nitrogen position in the pyridine substituent. The cooperativity estimated from the magnetic behaviour reflects their assembly nature.
CH16577Crystal Structure of a Heterometallic Luminophore: The RuII Complex of a Ferrocenyl-Terpyridine with a Flexible Linkage
Crystal structure determination on the mixed ligand complex [Ru(tpy)(L1)](ClO4)2 (tpy = 2,2′:6′,2″-terpyridine; L1 = 4′-(ferrocenylmethylaminomethylphenyl)terpyridine) shows the ferrocenyl group to be located as remotely as possible from the RuII centre. This may explain the fact that emission from the RuII centre is detectable even at room temperature in solution.
In this work, oxidative stress (OS) models of methanol in mice were successfully established. The experimental results clearly demonstrated that methanol could stimulate the production of hydroxyl radicals in the liver of mice to induce OS. Rhubarb and vitamin C were found to have a protective effect on the liver of mice under acute OS.
CH166011,2-Diaryl-1,2-disodioethanes: Versatile, Highly Reactive, and Tunable Synthetic Equivalents of Sodium Metal
1,2-Diaryl-1,2-disodioethanes are easily prepared, versatile, and tunable diorganometals finding application in 1,2-reductive eliminations as well as in the degradation of several persistent organic pollutants as homogeneous synthetic equivalents of a highly reactive form of Na metal. Further applications as dinucleophiles and bases are also described.
Electric field effects on the kinetics and thermodynamics of radical reactions have a significant, non-directional component arising in the increased polarizability of resonance-stabilized species.
CH16584Structural Systematics for Lanthanide(III) Systems: Interactions of the Achiral Hexamminecobalt(III) Cation with Tris(dipicolinato)lanthanate(III) Anions
Structures of [Co(NH3)6][Ln(dipic)3] hydrates have been analysed in terms of the weak interactions occurring between the achiral cation and the chiral anions.
CH16554Effective Dissolution of Biomass in Ionic Liquids by Irradiation of Non-Thermal Atmospheric Pressure Plasma
Lignocellulose has gained much interest as a potential renewable energy resource. However, it is hardly soluble. In this study, a non-thermal plasma was applied to dissolution of lignocellulose to ionic liquids. Chemically active species, which were generated by the plasma, induced decomposition of the lignin network, and consequently dissolution of biomass into ionic liquids was accelerated.
CH16537Dehydrogenative Coupling of Hydrosilanes and Alcohols by Alkali Metal Catalysts for Facile Synthesis of Silyl Ethers
The RO–H/H–Si cross-dehydrogenative coupling (CDC) of alcohols and hydrosilanes with high yield (up to 99 %) and chemoselectivity for the production of silyl ethers using alkali metal salts [MN(SiMe3)2] (M = Li, Na, K) as pre-catalysts and under ambient conditions is presented.
In this paper, we introduce a novel aptasensor for fast detection of oxytetracycline (OTC), based on a triple helix molecular switch (THMS) complex formation. The limit of detection (LOD) of this sensor was 1.67 and 6.44 nM in phosphate buffer and milk samples, respectively. The sensor also showed a high selectivity towards OTC.
CH16547Synthesis and Structures of Rare Earth 3-(4?-Methylbenzoyl)-propanoate Complexes – New Corrosion Inhibitors
A series of rare earth (RE) 3-(4′-methylbenzoyl)propanoate (mbp–) complexes [RE(mbp)3(H2O)] (RE = Y, La, Ce, Nd, Ho, Er) have been prepared by either metathesis reactions between the corresponding rare earth chloride and Na(mbp) or protolysis of rare earth acetates by the free acid.
CH16224Open-Chain Crown-Ether-Derived Two-Photon Fluorescence Probe for Real-Time Dynamic Biopsy of Mercury Ions
The probe developed in the present study can selectively detect Hg2+ ions in live cells and living tissues without interference from other metal ions and the membrane-bound probes, and its quenching constant is 8.73 × 105 M–1.
CH16357Ring-Opening Dispersion Polymerization of ʟ-Lactide with Polylactide Stabilizer in Supercritical Carbon Dioxide
The particle diameter distributions of PLLA show that the stabilizer S131 with short lipophilic segment could improve the particle diameter distribution range, compared with the long lipophilic segment of stabilizer S121. With increasing concentration of the stabilizer S131, the particle size decreased and particle distribution became narrow.
CH16460Improved Extraction Yield of Citral from Lemon Myrtle Using a Cellulose-Dissolving Ionic Liquid
The extraction yield of citral from lemon myrtle using cellulose-dissolving ionic liquids was up to 2.1 times higher than that obtained using ethanol. The ionic liquid could be recycled and reused nine times for the extraction of citral.
CH16527Coordination Behaviour of 1-(4,2′:6′,4′′-terpyridin-4′-yl)ferrocene and 1-(3,2′:6′,3′′-terpyridin-4′-yl)ferrocene: Predictable and Unpredictable Assembly Algorithms
1-(4,2′:6′,4″-Terpyridin-4′-yl)ferrocene offers a fixed V-shaped N,N″-donor set, but this does not lead to a predictable assembly algorithm; polymer and metalloamacrocycle formations compete. Similar competitive behaviour is observed in coordination assemblies based on 1-(4,2′:6′,4″-terpyridin-4′-yl)ferrocene, with the greater conformational flexibility of the latter adding to the non-predictability of the assembly process.
CH16392Synthesis and Characterisation of Hierarchically Porous HZSM-5 as Catalysts for the Synthesis of 2,3,5-Trimethyl-1,4-benzoquinone
Hierarchical HZSM-5 were synthesised by controlled desilication in alkaline medium and used as catalyst for the selective oxidation of 2,3,6-trimethylphenol to 2,3,5-trimethyl-1,4-benzoquinone. The combined studies suggested that the nature of the solvent, intrinsic acidity, and shape selectivity of the hierarchical structure ensured high catalytic properties.
An energetically viable pathway to the diterpene variediene is described. Only one of the three secondary carbocations along this pathway is predicted to be a minimum on the potential energy surface.
CH16347Synthesis and Evaluation of a Biocompatible Macromolecular Gadolinium Compound as a Liver-Specific Contrast Agent for MRI
Gadolinium complexes are widely applied as magnetic resonance imaging contrast agents. However, they have some undesirable properties, e.g. low relaxivity and target non-specificity. A new biocompatible macromolecular gadolinium compound has been synthesised as a liver-specific contrast agent. The ability to improve the imaging signal and the T1-relaxivity is satisfactory, and it has a long window imaging time with a low acute toxicity.
CH16488Cope Rearrangement in Bicyclo[5.1.0]octa-2,5-diene and its Mono- and Di-Hetero Analogues: A DFT Study
Cope rearrangement of bicycle[5.1.0]octa-2,5-diene and its 8-hetero- (N,O,P) and 4,8-dihetero-analogues has been investigated in the gas phase at the B3LYP/6-31+G* level. The results reveal that relative stabilities of the three-membered ring undergoing opening and the three-membered ring being formed as a result of the Cope rearrangement determine the feasibility and rate of the rearrangement.
CH16398A New Fluorometric Method for the Determination of Oxaliplatin Based on Cucurbituril Supramolecular Interaction
The fluorescence intensity of CB–PAL, CB–BER, or CB–COP system decreased with increasing amounts of oxaliplatin (l-OHP) added. The trend is attributed to the competition between l-OHP and PAL, BER, or COP molecules for occupancy of the CB cavity.
CH16406A Quantum Theory of Atoms-in-Molecules Perspective and DFT Study of Two Natural Products: Trans-Communic Acid and Imbricatolic Acid
Intramolecular H···H as well as C···H non-covalent interactions have been retrieved and characterized using quantum theory of atoms-in-molecules and the computed chemical reactivity index using HOMO–LUMO gap and molecular electrostatic potential surface have been compared with experimentally observed bioactivity parameter.
CH16288Preparation and Characterization of PA6-PEG/Li High Performance Static Dissipation Composites
A series of novel PA6-PEG/Li composites were developed by melt blending the PA6-PEG copolymer (10 wt-% PEG) with three different kinds of colourless lithium salts (LiCl, C18H35LiO2, LiAc). The PA6-PEG/LiCl composite showed an excellent static dissipation performance of 2.71 × 108 Ω square–1.
The influence of organic backbone on the bonding modes of the dicarboxylates, conformations of the of the long and flexible dipyridyl ligand, and pore size in isoreticular metal–organic frameworks formed by three double pillared-layer CoII metal–organic frameworks with a pcu topology is discussed.
CH16364A Green and Convenient Route for the Regioselective Synthesis of New Substituted 3-Aryl-5H-indeno[1,2-c]pyridazines as Potential Monoamine Oxidase Type A Inhibitors
Several indeno[1,2-c]pyridazines were efficiently synthesised using the one-pot, three-component reaction of substituted indanones, arylglyoxalmonohydrates, and hydrazine in the presence of 1,5-diazabicyclo[4,3,0]non-5-ene (DBN) in water at room temperature.
CH16459Synthesis of a Tetraphenylethene-Substituted Tetrapyridinium Salt with Multifunctionality: Mechanochromism, Cancer Cell Imaging, and DNA Marking
A tetrapyridyl-substituted tetraphenylethylene (TPy-TPE) works as a good fluorescent visualiser for specific staining for cellular imaging and as a DNA marker.
CH16454Effect of Hydrogen Peroxide on the Extraction of Components of Cedar Powder with Tetrabutylphosphonium Hydroxide Aqueous Solution at 60°C
Cedar powder was treated with ionic liquids and onium hydroxide aqueous solution under very mild condition such as at 60°C. Addition of hydrogen peroxide accelerated the dissolution of lignin fragments with larger molecular weights owing to scission of the lignin network structure.
CH16368Two 3D ZnII Metal–Organic Frameworks with 3- and 8-Fold Interpenetration: Syntheses, Structures, Photodegradation, and Photoluminescent Properties
Two novel zinc coordination polymers have been synthesised and characterised. Their topological structures show 4-connected 8- and 3-fold interpenetrating 3D frameworks. Furthermore, they exhibit good photodegradation capability and photoluminescence properties.
CH16138Effect of Alkyl Chain Length of Imidazolium Cation on the Electroreduction of CO2 to CO on Ag Electrode in Acetonitrile
Effect of imidazolium cation (MIM+) on the electroreduction of CO2 to CO was investigated by linear sweep voltammetry (LSV), cyclic voltammetry (CV), constant potential electrolysis (CPE), and density functional theory (DFT) computations. It is interesting to find that the catalytic effect of MIM+ is sensitive to the alkyl chain length on its N1-position.
Various glycosylation reactions were tried in an effort to synthesise β-linked tutin glycosides, found in toxic honeys. Cationic palladium-mediated glycosylation gave the α-linked tutin tetrabenzyl glucoside (5 : 1, α : β). Hydrogenolysis of the benzyl ether groups resulted in tutin double-bond migration. Epoxide opening and rearrangement were observed upon acetylation of the tutin glucoside.
A polyglycidyl methacrylate electrospun scaffold was fabricated encapsulating a lipophilic drug, PXS64. Efficacy of the developed scaffold was explored for skin scar therapy applications.
CH16333Syntheses and Characterizations of Three Organically Templated Zinc Phosphites with 12-Ring Channels
Three zinc phosphites have been synthesized and characterized. Their frameworks are constructed from 4-connected ZnO4 tetrahedra and 3-connected HPO3 pseudopyramids. There are 12-membered ring (12-MR) and 8-MR apertures in their (3,4)-connected network. Helical chains are observed in compound 3.
CoWO4/g-C3N4 was synthesized by precipitation and calcination, and used as a catalyst for oxidative desulfurization. In the process, CoWO4/g-C3N4 showed excellent desulfurization activity and the desulfurization rate reached 92.9 %. Moreover, the catalyst could be recycled at least five times without any clear decrease in catalytic activity.
CH16467Endocyclic and Endo–Exocyclic Silver(I) Complexes of Thiaoxaaza Macrocycles: Crystallographic and NMR Studies
Thiaoxaaza macrocycles incorporating NO2S2 (L1) and NO2S3 (L2) donors were employed and their silver(i) nitrate complexation in solid and solution states was investigated.
The construction of the first Salen-type 3D lanthanide complex using Salen ligands and mixed lanthanide counter-ions is described.
CH16236Novel SrO-CaO Mixed Metal Oxides Catalyst for Ultrasonic-Assisted Transesterification of Jatropha Oil into Biodiesel
Novel strontium oxide/calcium oxide (SrO-CaO) mixed metal oxides heterogeneous catalyst is synthesized to highlight its catalytic potential for the transformation of Jatropha oil to green biofuels via an ultrasonic-assisted transesterification process.
CH16180Synthesis of a Novel Dibenzylamide Derivative of p-tert-Octylcalixarene and its Extraction Properties Towards Noble Metal Ions
A N,N-dibenzylacetoamide derivative of p-tert-octylcalixarene has been synthesised and its solvent extraction of precious metals in nitric acid media was investigated for determining the effects of extractant concentration and its contact time as well as nitric acid concentration in comparison with a N,N-diethylacetoamide derivative.
CH16200Oxidative N-Dealkylation of Tertiary Amines with Tetraethylammonium Periodate Catalyzed by Metal Complexes
Oxidative N-dealkylation of tertiary amines with tetraethyl ammonium periodate led to formation of corresponding N-dealkylated and mono-oxygenated products. One electron transfer dominates over hydrogen abstraction in the reaction mechanism.
CH16165Computational Studies on the Encapsulation of 1,4-Dihydropyridine Derivatives into CNT(10,10)
This paper investigates the use of (10,10) armchair carbon nanotube (CNT(10,10)) as a new drug delivery system for 1,4-dihydropyridine derivatives.
CH16250Preparation of Magnetic Surface-Imprinted Polymer Microspheres with Hydrophilic External Layers for Selective Extraction of Fluoroquinolones from Eggs
Novel restricted access media–molecularly imprinted magnetic microspheres that displayed water-compatibility, exclusion of biomacromolecules, and selective enrichment of analytes were prepared by a one-pot surface imprinting method for the magnetic dispersion microextraction of trace fluoroquinolones from egg samples.
Although PhI(OAc)2 is known as an oxidizing agent, it can also serve as a reagent or a catalyst in different types of chemical reactions in organic synthesis. PhI(OAc)2 is used in radical reactions, oxidation reactions, and in heterocycle synthesis. This paper reports some relevant and recent new uses of PhI(OAc)2.
CH16344Preparation and UCST-Type Phase Behaviours of Poly(γ-4-methylbenzyl-L-glutamate) Pyridinium Tetrafluoroborate Conjugates in Methanol or Water
Poly(γ-4-methylbenzyl-L-glutamate) pyridinium tetrafluoroborate conjugates with constant main chain length, various pyridinium pendants, and high grafting efficiency can be readily prepared by nucleophilic substitution and ion-exchange reaction. They can exhibit reversible UCST-type phase behaviours in both methanol and water depending on the type of pyridinium pendants.
These articles have been peer reviewed and accepted for publication. They are still in production and have not been edited, so may differ from the final published form.
Two new Oxovanadium(IV) Compounds containing Amino Acid Schiff Base and 1,10-bathophenanthroline Ligands: Syntheses, Crystal Structures and in vitro Evaluation of the Anticancer Activities
An experimental and theoretical study on reaction mechanism and molecular structure of 4-(diphenylamino)-3-iodofuran- 2(5H)-one
Perspective view of Metal Organic Frameworks and other existing materials as a drug delivery carrier
Synthesis and characterization of Co1-xCuxFe2-xAlxO4 ferrite nano-scales as a potential candidate for high density data storage applications
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