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Item Metadata only 1,2,3-triazoles in peptidomimetic chemistry(Wiley-V C H Verlag GMBH, 2011) Pedersen, D.; Abell, A.The ability to synthesise small peptidomimetics that mimic the secondary structure of proteins is an ever expanding area of research directed at sourcing new medicinal agents and biological probes. A significant current challenge is to mimic protein epitopes under physiological conditions using small peptidomimetics that are easy to prepare. The copper- and ruthenium-catalysed Huisgen cycloaddition reactions provide such a general synthetic method, with the resulting 1,2,3-triazoles being good peptide bond mimics. The ability to prepare both 1,4- and 1,5-substituted 1,2,3-triazoles under these chemically benign conditions provides both “linear” and “bent” peptidomimetics. Examples of the use of 1,2,3-triazoles to define the geometry and properties of a peptidomimetic abound. This review highlights such successes but also describes a number of failures in order to guide and inspire future efforts of chemists in this area.Item Metadata only 1,2,3-Triazolyl amino acids as AMPA receptor ligands(Pergamon-Elsevier Science Ltd, 2010) Stanley, N.; Pedersen, D.; Nielsen, B.; Kvist, T.; Mathiesen, J.; Brauner-Osborne, H.; Taylor, D.; Abell, A.The central nervous system glutamate receptors are an important target for drug discovery. Herein we report initial investigations into the synthesis and glutamate receptor activity of 1,2,3-triazolyl amino acids. Two compounds were found to be selective AMPA receptor ligands, which warrant further investigation.Item Metadata only 1,2-dioxines as masked cis γ-hydroxy enones and their versatility in the synthesis of highly substituted γ-lactones(Amer Chemical Soc, 2002) Greatrex, B.; Kimber, M.; Taylor, D.; Fallon, G.; Tiekink, E.Addition of highly stabilized ester nucleophiles to 1,2-dioxines affords good to high yields of γ-lactones with high diastereoselectivity. Heterolytic or homolytic cleavage of the 1,2-dioxines under appropriate conditions generates the key reactive cis γ-hydroxy enones, which ultimately afford the observed γ-lactones. Diastereoselectivity is installed as a result of anti 1,4-addition by the ester enolate to the cis enones followed by intramolecular cyclization. The reaction is tolerant of a range of substitution patterns on the 1,2-dioxine while a broad range of esters are also accommodated. In addition to the synthesis of racemic γ-lactones, highly enantioenriched γ-lactones can also be synthesized when chiral cobalt(II) catalysts are employed for the initial homolytic ring-opening of the 1,2-dioxine.Item Metadata only 1,2-dioxines containing tethered hydroxyl functionality as convenient precursors for pyran syntheses(Amer Chemical Soc, 2005) Avery, T.; Caiazza, D.; Culbert, J.; Taylor, D.; Tiekink, E.A new method for the construction of tetrahydropyrans derived from readily available 1,2-dioxines containing a tethered hydroxyl moiety is described. The reaction proceeds via a base-catalyzed rearrangement of the 1,2-dioxines to either the isomeric cis or trans -hydroxy enones followed by intramolecular oxa-Michael addition of the tethered hydroxyl group.Item Metadata only (1,3-Benzo[d]dioxol-5-yl)(2-pyridyl)methyl cyanide(International Union of Crystallography, 2001) Duthie, Andrew; Scammells, Peter J.; Katsifis, Andrew; Tiekink, Edward Richard Tom; School of Chemistry and PhysicsIn the title compound, C₁₄H₁₀N₂O₂, the dihedral angle formed between the substituted pyridine ring and 1,3-benzodioxole group is 67.73 (6)°. The crystal features chains of molecules held together by alternating π⋯π and C—H⋯π interactions.Item Metadata only 1,3-Bis[(trimethylsilylmethyl)dichlorostannyl]propane,[(Me₃SiCH₂)Cl₂Sn]₂(CH₂)₃)(John Wiley & Sons, 2003) Dakternieks, Dainis; Kuan, Fong Sheen; Duthie, Andrew; Tiekink, Edward Richard Tom; School of Chemistry and PhysicsItem Metadata only 1,4-bis[(phenyldichlorostannyl)ethyl]benzene, p-(Cl2PhSnCH2CH2)2C6H4(John Wiley & Sons Ltd, 2003) Dakternieks, Dainis; Duthie, Andrew; Tiekink, Edward Richard Tom; School of Chemistry and PhysicsItem Metadata only 1,4-Bis[bis(trimethylsilyl)methyl- dichlorostannylmethyldimethylsilyl]benzene, p-{[(Me3Si)2CH]Sn(Cl)2CH2SiMe2}2C6H4(John Wiley & Sons Ltd, 2003) Dakternieks, Dainis; Zobel, Bernhard; Tiekink, Edward Richard Tom; School of Chemistry and PhysicsItem Metadata only 1,4-Diethynyl-2,5-dimethoxybenzene at ca 150 K(Blackwell Munksgaard, 2004) Bruce, M.; Head, N.; Skelton, B.; White, A.The principal determinants of packing in crystals of the title compound, C12H10O2, which has crystallographically imposed inversion symmetry, are interactions between the alkyne H atoms and the methoxy O atoms [HO = 2.39 (1) Å].Item Metadata only 1-Bromoethene-1-sulfonyl fluoride (BESF) is another good connective hub for SuFEx click chemistry(Royal Society of Chemistry (RSC), 2018) Smedley, C.J.; Giel, M.C.; Molino, A.; Barrow, A.S.; Wilson, D.J.D.; Moses, J.E.We demonstrate 1,2-dibromoethane-1-sulfonyl fluoride (DESF) as a bench-stable and readily accessible precursor to the robust SuFEx connector, 1-bromoethene-1-sulfonyl fluoride (BESF). The in situ generation of BESF from DESF opens up several new reaction profiles, including application in the syntheses of unprecedented 3-substituted isoxazole-5-sulfonyl fluorides, 1-substituted-1H1,2,3-triazole-4-sulfonyl fluorides, 2-amino-1-bromoethane-1-sulfonyl fluorides and 4-bromo-b-sultams in good to excellent yields. These new modules comprise a pendant sulfonyl fluoride handle, which further undergoes facile and selective SuFEx reactions with a selection of aryl silyl ethers to generate stable and useful sulfonate connections.Item Metadata only 11-Hydroxy-3,3-dimethyl-7,12-dioxo-3,4,6,6a,7,12,12a,12b-octahydrobenz[a]anthracen-1-yl acetate(Munksgaard Int Publ Ltd, 2003) Rozek, T.; Bowie, J.; Skelton, B.; White, A.The Diels-Alder reaction between 5-hydroxy-1,4-naphthoquinone and 5,5-dimethyl-3-vinyl-1,2-cyclohexadienyl acetate by endo addition gives the title compound, C(22)H(22)O(5), in 68% yield. This racemic diastereoisomer has the opposite regiochemistry to ochromycinone analogues produced previously and may allow access to a new type of anticancer-active saquayamycin analogue.Item Metadata only (2,2 ': 6 ',2 ''-Terpyridine)platinum(II) complexes containing (thioalkyl)dicarba-closo-dodecaborane(12) ligands(American Chemical Society, 2005) Todd, Jean Ann; Turner, Peter David; Ziolkowski, Erin J.; Rendina, Louis M.; School of Chemistry and Physics; School of Chemistry and Physics : ChemistryItem Metadata only 2,4,5-Triphenylisothiazol-3(2H)-one 1,1-dioxides as inhibitors of human leukocyte elastase.(Informa Healthcare, 2005) Gutschow, M.; Pietsch, M.; Themann, A.; Fahrig, J.; Schulze, B.A series of substituted 2,4,5-triphenylisothiazol-3(2H)-one 1,1-dioxides 9 was synthesized and investigated as inhibitors of human leukocyte elastase (HLE). All compounds were found to inhibit HLE in a time-dependent manner and most of them exhibited kobs/[I] values > 300 M− 1s− 1. The most potent 3-oxosultam of this series was 9l (kobs/[I] = 2440 M− 1s− 1). Kinetic investigations performed with 9g and different substrate concentrations did not allow to clearly distinguish between a competitive or noncompetitive mode of inhibition. A more complex interaction is supported by the failure of a linear dependency of kobs values on the inhibitor concentration.Item Metadata only (±)-2,5-Dioxoperhydrocycloocta[b]furan-3-carboxylic acid(Blackwell Munksgaard, 2002) Greatrex, B.; Kimber, M.; Taylor, D.; Fallon, G.The anti stereochemistry between the fused rings of the bicyclic lactone (±)-2,5-dioxoperhydrocycloocta[b]furan-3-carboxylic acid, C₁₁H₁₄O₅, has been established. Intermolecular hydrogen bonds are observed between the carboxylic acid group and the carbonyl O atom of an adjacent molecule.Item Metadata only 2-(6-fluoro-5-hydroxy-2-methyl-1H-3-indenyl)acetic acid(International Union of Crystallography, 2001) Razzino, Pasquale; Ward, Arthur David; Tiekink, Edward Richard Tom; School of Chemistry and Physics : ChemistryItem Metadata only 2-(N-Acetylamino)pent-4-ynamide(1998) Crisp, Geoffrey T.; Jiang, Yu-Lin; Tiekink, Edward Richard Tom; School of Chemistry and Physics; School of Chemistry and Physics : ChemistryItem Metadata only 2-C-Cyclohexyl-2,3-O-isopropylideneerythrofuranose(Blackwell Munksgaard, 2009) Robinson, T.; Taylor, D.; Tiekink, E.In the title compound, C(13)H(22)O(4), the acetonide ring adopts an envelope conformation with one of the O atoms as the flap atom, whereas a twisted conformation is found for the furan-ose ring. Centrosymmetric eight-membered {⋯OCOH}(2) synthons involving the hydr-oxy H and acetonide O atoms are found in the crystal structure. These are linked into a supra-molecular chain in the a-axis direction via C-H⋯O contacts.Item Metadata only 2-C-Phenylerythrono-1,4-lactone(Blackwell Munksgaard, 2009) Robinson, T.; Taylor, D.; Tiekink, E.The title compound (systematic name
3,4-dihydr-oxy-3-phenyl-furan-2-one), C(10)H(10)O(4), features a five-membered γ-lactone ring with an envelope conformation at the C atom carrying the hydr-oxy group without the phenyl substituent. In the crystal, supra-molecular chains mediated by O-H⋯O hydrogen bonding are formed along the a-axis direction. These are consolidated in the crystal structure by C-H⋯O contacts.Item Metadata only 2-D Coordination Polymers of Hexa(4-cyanophenyl)[3]-radialene and Silver(I): Anion•••π-Interactions and Radialene C−H•••Anion Hydrogen Bonds in the Solid-State Interactions of Hexaaryl[3]-radialenes with Anions(American Chemical Society, 2009) Hollis, C.; Hanton, L.; Morris, J.; Sumby, C.As part of our studies of ligands containing an electron-deficient [3]-radialene core we discovered that the hexadentate ligand hexa(4-cyanophenyl)[3]-radialene 1 forms 6,3-connected 2-D coordination polymers on reaction with silver(I). Compounds {[Ag(1)](PF6) · 2(CH3NO2)}n 2 and {[Ag(1)](ClO4) · 2(CH3NO2)}n 3, which are the first coordination polymers of 1, readily crystallize from solutions of the silver salt and 1 in noncoordinating nitromethane solvent and were characterized by X-ray crystallography. In these structures the ligand is hypodentate, coordinating only through four nitrile N-donors to act as a 3-connecting center. The distorted tetrahedral silver also acts as a 3-connecting center. In the extended structure the anions lie in pockets above and below the [3]-radialene core of the ligands, forming moderate and weak hydrogen bonds with four different molecules of 1. The anions are in close proximity to the electron-deficient [3]-radialene core of 1, forming weak anion-π interactions.Item Metadata only 2-Hydroxy-5-[(E)-(4-methoxyphenyl)-diazenyl]benzoic acid(Blackwell Publishing on behalf of the International Union of Crystallography, 2000) Basu Baul, Tushar S.; Dhar, Sushmita; Tiekink, Edward Richard Tom; School of Chemistry and PhysicsThe title compound, C₁₄H₁₂N₂O₄, shows an E conformation about the diazenyl N atoms. The crystal structure features layers of molecules with the primary connection between the layers afforded by carboxylic acid dimer motifs; no evidence for extensive π–π stacking between the layers was found.