Publications
179 results found
Abas H, Linsdall SM, Mamboury M, et al., 2017, Total Synthesis of (+)-Lophirone H and Its pentamethyl ether utilizing an oxonium-prins cyclization, Organic Letters, Vol: 19, Pages: 2486-2489, ISSN: 1523-7052
The first total synthesis of (+)-lophirone H (1) and its pentamethyl ether 29, featuring an oxonium–Prins cyclization/benzylic cation trapping reaction, is described.
Murray JI, Flodén NJ, Bauer A, et al., 2017, Kinetic Resolution of 2-Substituted Indolines by N -Sulfonylation using an Atropisomeric 4-DMAP- N -oxide Organocatalyst, Angewandte Chemie, Vol: 129, Pages: 5854-5858, ISSN: 0044-8249
The first catalytic kinetic resolution by N‐sulfonylation is described. 2‐Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4‐dimethylaminopyridine‐N‐oxide (4‐DMAP‐N‐oxide) organocatalyst. Use of 2‐isopropyl‐4‐nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.
Murray JI, Floden NJ, Bauer A, et al., 2017, Kinetic resolution of 2-substituted indolines by N-sulfonylation using an atropisomeric 4-DMAP-N-oxide organocatalyst, Angewandte Chemie International Edition, Vol: 56, Pages: 5760-5764, ISSN: 1433-7851
The first catalytic kinetic resolution by N-sulfonylation is described. 2-Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4-dimethylaminopyridine-N-oxide (4-DMAP-N-oxide) organocatalyst. Use of 2-isopropyl-4-nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.
Frampton CS, Murray JI, Spivey AC, 2017, Crystal structure of 1-methylimidazole 3-oxide monohydrate., Acta Crystallographica Section E: Crystallographic Communications, Vol: 73, Pages: 372-374, ISSN: 2056-9890
1-Methylimidazole 3-N-oxide (NMI-O) crystallizes as a monohydrate, C4H6N2O·H2O, in the monoclinic space group P21 with Z' = 2 (mol-ecules A and B). The imidazole rings display a planar geometry (r.m.s. deviations = 0.0008 and 0.0002 Å) and are linked in the crystal structure into infinite zigzag strands of ⋯NMI-O(A)⋯OH2⋯NMI-O(B)⋯OH2⋯ units by O-H⋯O hydrogen bonds. These chains propagate along the b-axis direction of the unit cell.
Bodero O, Spivey AC, 2016, An expedient synthesis of 2-aryl-1,4-benzoxazin-3-ones via tandem Anionic cyclisation/alkylation reactions of N-Boc-O-benzyl-2-aminophenols, Synlett, Vol: 27, ISSN: 0936-5214
A one-pot, tandem anionic cyclization/alkylation reaction of N-Boc-O-benzylated-2-aminophenols to give 2-aryl-1,4-benzoxazin-3-ones is described. The Boc protecting group plays a crucial role in the process, as the tert-butoxide liberated in the cyclisation step facilitates the benzylic deprotonation necessary for the subsequent alkylation. The reaction gives expedient access to a range of substitution patterns in 1,4-benzoxazin-3-ones of potential biological relevance.
Murray JI, Spivey AC, 2016, Preparation of 1-Methylimidazole- N-oxide (NMI-O), ORGANIC SYNTHESES, Vol: 93, Pages: 331-+, ISSN: 0078-6209
Abas H, Frampton CS, Spivey AC, 2016, Diels-Alder Reactions of α-Amido Acrylates with N-Cbz-1,2-dihydropyridine and Cyclopentadiene, Journal of Organic Chemistry, Vol: 81, Pages: 9947-9956, ISSN: 1520-6904
Thermal Diels-Alder reactions of α-amido acrylates with N-Cbz-1,2-dihydropyridine and cyclopentadiene have been explored to investigate the factors influencing the endo/exo selectivity. For the dihydropyridine, steric factors allowed the diastereoselectivity to be modulated to favor either endo- or exo-ester adducts. For cyclopentadiene, the endo-ester adducts were favored regardless of steric perturbation, although catalysis by bulky Lewis acids increased the proportion of exo-ester adducts in some cases. These Lewis acids were incompatible with the dihydropyridine diene as they induced its decomposition.
Murray JI, Heckenast Z, Spivey AC, 2016, Chiral Lewis Base Activation of Acyl and Related Donors in Enantioselective Transformations (n → π*), Lewis Base Catalysis in Organic Synthesis, Pages: 457-526, ISBN: 9783527336180
The role of Lewis bases in acylation reactions has been studied from both synthetic and mechanistic standpoints with a particular recent focus on enantioselective variants mediated by single enantiomer chiral Lewis bases deployed substoichiometrically. The modern-era of research into asymmetric enantioselective nucleophile-catalyzed acyl transfer using designed nucleophiles was initiated in the mid-1990s by the groups of Vedejs and Fu. This group developed chiral ferro-cenyl 4-dialkylaminopyridine derivatives first for the kinetic resolution (KR) of sec-alcohols and for an array of other transformations. Since the 1980s, the synthetic potential of enantioselective acylation has been well established in the context of fine chemical synthesis as a result of the development of biocatalytic processes that rely on hydrolytic enzymes. Cognizant that both bases and nucleophiles catalyze the acylation of alcohols using anhydrides and that alkyl phosphines in particular display weak basicity and strong nucleophilicity, Vedejs and Diver published a study of the utility of phosphines as acyl transfer catalysts.
Almond-Thynne J, Blakemore DC, Pryde DC, et al., 2016, Site-selective Suzuki-Miyaura coupling of heteroaryl halides - understanding the trends for pharmaceutically important classes, Chemical Science, Vol: 8, Pages: 40-62, ISSN: 2041-6539
Suzuki–Miyaura cross-coupling reactions of heteroaryl polyhalides with aryl boronates are surveyed. Drawing on data from literature sources as well as bespoke searches of Pfizer's global chemistry RKB and CAS Scifinder® databases, the factors that determine the site-selectivity of these reactions are discussed with a view to rationalising the trends found.
Spivey A, 2016, Lewis-base catalysis of asymmetric acylation, sulfonylation, and phosphorylation processes, Publisher: AMER CHEMICAL SOC, ISSN: 0065-7727
Murray JI, Spivey AC, 2015, Amines <i>vs</i>. <i>N</i>-Oxides as Organocatalysts for Acylation, Sulfonylation and Silylation of Alcohols: 1-Methylimidazole <i>N</i>-Oxide as an Efficient Catalyst for Silylation of Tertiary Alcohols, ADVANCED SYNTHESIS & CATALYSIS, Vol: 357, Pages: 3825-3830, ISSN: 1615-4150
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- Citations: 25
Carroll L, Evans H, Spivey AC, et al., 2015, Mn-salen catalysed benzylic C-H activation for the synthesis of aryl [(18)F]CF3-containing PET probes., Chemical Communications, Vol: 51, Pages: 8439-8441, ISSN: 1364-548X
The development of a Mn-salen complex catalysed oxidative benzylic fluorination of non-activated C-H bonds using [(18)F]fluoride is described for installation of [(18)F]CHRF, [(18)F]CR2F and particularly [(18)F]CF3 containing groups in the presence of other functional groups.
Murray JI, Woscholski R, Spivey AC, 2015, Organocatalytic Phosphorylation of Alcohols Using Pyridine-N-oxide, Synlett, Vol: 26, Pages: 985-990, ISSN: 1437-2096
Murray JI, Woscholski R, Spivey AC, 2014, Highly efficient and selective phosphorylation of amino acid derivatives and polyols catalysed by 2-aryl-4-(dimethylamino)pyridine-<i>N</i>-oxides - towards kinase-like reactivity, CHEMICAL COMMUNICATIONS, Vol: 50, Pages: 13608-13611, ISSN: 1359-7345
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- Citations: 41
Evans HL, Quang-De N, Carroll LS, et al., 2014, A bioorthogonal <SUP>68</SUP>Ga-labelling strategy for rapid <i>in vivo</i> imaging, CHEMICAL COMMUNICATIONS, Vol: 50, Pages: 9557-9560, ISSN: 1359-7345
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- Citations: 55
Evans HL, Carroll L, Aboagye EO, et al., 2014, Bioorthogonal chemistry for <SUP>68</SUP>Ga radiolabelling of DOTA-containing compounds, JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, Vol: 57, Pages: 291-297, ISSN: 0362-4803
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- Citations: 20
Pisaneschi F, Slade RL, Iddon L, et al., 2014, Synthesis of a new fluorine-18 glycosylated 'click' cyanoquinoline for the imaging of epidermal growth factor receptor, JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, Vol: 57, Pages: 92-96, ISSN: 0362-4803
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- Citations: 8
George GPC, Stevens E, Aberg O, et al., 2014, Preclinical evaluation of a CXCR4-specific <SUP>68</SUP>Ga-labelled TN14003 derivative for cancer PET imaging, BIOORGANIC & MEDICINAL CHEMISTRY, Vol: 22, Pages: 796-803, ISSN: 0968-0896
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- Citations: 19
Andrews KG, Spivey AC, 2013, Improving the Accuracy of Computed <SUP>13</SUP>C NMR Shift Predictions by Specific Environment Error Correction: Fragment Referencing, JOURNAL OF ORGANIC CHEMISTRY, Vol: 78, Pages: 11302-11317, ISSN: 0022-3263
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- Citations: 22
Andrews KG, Frampton CS, Spivey AC, 2013, Structural assignment of a bis-cyclopentenyl--cyanohydrin formed via alkene metathesis from either a triene or a tetraene precursor, ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, Vol: 69, Pages: 1207-+, ISSN: 2053-2296
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- Citations: 4
Carroll L, Evans HL, Aboagye EO, et al., 2013, Bioorthogonal chemistry for pre-targeted molecular imaging - progress and prospects, ORGANIC & BIOMOLECULAR CHEMISTRY, Vol: 11, Pages: 5772-5781, ISSN: 1477-0520
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- Citations: 59
Sejberg JJP, Smith LD, Leatherbarrow RJ, et al., 2013, Enantioselective synthesis of (+)-aspercyclide A, TETRAHEDRON LETTERS, Vol: 54, Pages: 4970-4972, ISSN: 0040-4039
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- Citations: 8
Bayly AR, White AJP, Spivey AC, 2013, Design and Synthesis of a Prototype Scaffold for Five-Residue -Helix Mimetics, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Vol: 2013, Pages: 5566-5569, ISSN: 1434-193X
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- Citations: 10
Srikaran R, Kontorgiorgis CA, Warren SA, et al., 2013, Synthesis of a 4-Aryl-2-anilinopyrimidine Using a Germanium-Functionalised Non-Cross-Linked Polystyrene (NCPS) Support, SYNLETT, Vol: 24, Pages: 1663-1666, ISSN: 0936-5214
Smith LD, Leatherbarrow RJ, Spivey AC, 2013, Development of small molecules to target the IgE:FcεRI protein-protein interaction in allergies, FUTURE MEDICINAL CHEMISTRY, Vol: 5, Pages: 1423-1435, ISSN: 1756-8919
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- Citations: 8
George GPC, Pisaneschi F, Stevens E, et al., 2013, Scavenging strategy for specific activity improvement: application to a new CXCR4-specific cyclopentapeptide positron emission tomography tracer, J. Label Compd. Radiopharm.
Huisgen cycloaddition is attractive to label peptide because of its rapidity and bioorthogonality. However, for larger tracers, the physico-chemical differences between the precursor and the tracer are usually insufficient to allow their separation by HPLC, reducing the specific activity. This is of importance for peptidic tracers because the combination of their high-affinity receptor with low specific activity results in the precursor saturating the receptors, causing non-specific tracer binding. Here, we report a fast, one-pot, general strategy to circumvent this issue, yielding a tracer of improved specific activity. It consists in adding a lipophilic azide after the labeling step to scavenge unreacted precursor into a more lipophilic species that does not co-elute with the tracer. We applied this strategy to a new fluorinated cyclopentapeptidic CXCR4 antagonist for the PET imaging of cancer, CCIC15, for which we managed to reduce the apparent peptide concentration by a factor of 34 in 10 min. This tracer was radiolabeled by click chemistry with 2-[18F]fluoroethylazide, yielding the tracer in 18 ±6% (n = 5) end-of-synthesis radiochemical yields (EOS-RCY) in 1.5 h from [18F]fluoride with a specific activity of 19.4 GBq μmol 1. Preliminary biological evaluation of the probe confirmed potency and specificity for CXCR4; further biological evaluation is underway.
Murray JI, Spivey AC, Woscholski R, 2013, Alternative synthetic tools to phospho-specific antibodies for phosphoproteome analysis: progress and prospects., J Chem Biol, Vol: 6, Pages: 175-184, ISSN: 1864-6158
Signal transduction cascades in living systems are often controlled via post-translational phosphorylation and dephosphorylation of proteins. These processes are catalyzed in vivo by kinase and phosphatase enzymes, which consequently play an important role in many disease states, including cancer and immune system disorders. Current techniques for studying the phosphoproteome (isotopic labeling, chromatographic techniques, and phosphospecific antibodies), although undoubtedly very powerful, have yet to provide a generic tool for phosphoproteomic analysis despite the widespread utility such a technique would have. The use of small molecule organic catalysts that can promote selective phosphate esterification could provide a useful alternative to current state-of-the-art techniques for use in, e.g., the labeling and pull-down of phosphorylated proteins. This report reviews current techniques used for phosphoproteomic analysis and the recent use of small molecule peptide-based catalysts in phosphorylation reactions, indicating possible future applications for this type of catalyst as synthetic alternatives to phosphospecific antibodies for phosphoproteome analysis.
Evans HL, Carroll L, Nguyen Q-D, et al., 2013, Copper-free 'click' chemistry as a potential pre-targeting tool for PET imaging, JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, Vol: 56, Pages: S204-S204, ISSN: 0362-4803
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- Citations: 1
George GPC, Stevens E, Pisaneschi F, et al., 2013, Synthesis, radiolabelling and biological evaluation of new PET probes for CXCR4-specific imaging, JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, Vol: 56, Pages: S409-S409, ISSN: 0362-4803
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- Citations: 1
Webber MJ, Warren SA, Grainger DM, et al., 2013, Towards the enantioselective synthesis of (-)-euonyminol - preparation of a fully functionalised lower-rim model, ORGANIC & BIOMOLECULAR CHEMISTRY, Vol: 11, Pages: 2514-2533, ISSN: 1477-0520
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- Citations: 17
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