283 results for Brimble, Margaret

  • Synthesis and biological evaluation of the osteoblast proliferating cyclic peptides dianthins G and H

    Kaur, Harveen; Heapy, AM; Kowalczyk, Renata; Amso, Z; Watson, Maureen; Cornish, Jillian; Brimble, Margaret (2014-10-21)

    Journal article
    The University of Auckland Library

    The first synthesis and osteoblast proliferative activity of the naturally occurring cyclic peptides dianthins G and H is described. The greater potency of naturally occurring dianthin G over dianthin H at physiological concentrations mirrored the osteoblast proliferative activity observed for synthetic dianthins G and H. Six alanine-scan analogues of the more potent dianthin G were also synthesised and osteoblast assays revealed that four of the six residues can be further modified for improved activity. We also confirmed by variable temperature 1H NMR spectroscopic analysis that the sets of major and minor signals observed for dianthins G and H in DMSO-d6 are in fact due to cis???trans rotational isomers of the proline ring.

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  • Review of book Science of Synthesis, Volume 28: Compounds with Two Carbon-Heteroatom Bonds: Quinones and Heteroatom Analogues, by A. G. Griesbeck

    Brimble, Margaret (2007)

    Unclassified
    The University of Auckland Library

    Volume 28, Quinones and Heteroatom Analogues comprises part of the highly esteemed reference work Science of Synthesis, Houben???Weyl Methods of Molecular Transformations that consists of 48 planned volumes and is already an essential tool for modern retrieval of reliable synthetic information. Volume 28 covers modern synthetic methods to prepare quinones and their heteroatom analogues, and is one of nine volumes comprising Category 4 (Compounds with Two Carbon???Heteroatom Bonds). ...

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  • Neural Regeneration Peptides and Methods for their Use

    Sieg, F; Brimble, Margaret; Muir, Victoria (2010-05-27)

    Patent
    The University of Auckland Library

    Embodiments of this invention include novel peptides that can promote survival of neurons and other cell types. Other embodiments of this invention include the methods for the use of peptides to promote neuronal migration, neurite outgrowth, neuronal proliferation, neural differentiation, neuronal survival and/or trophoblast proliferation, trophoblast migration and trophoblase survival. NRP compounds may be administered directly to a subject or to a subject's cells by a variety of means including orally, intraperitoneally, intravascularly or indirectly via a replicable vehicle. NRP compounds can be formulated into pharmaceutically acceptable dosage forms for therapeutic use. Kits containing pre-determined doses of an NRP can be used to conveniently store, prepare and administer an NRP to a subject in need thereof.

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  • Chemistry Research: Making Molecules for Medicines

    Brimble, Margaret (2008)

    Book item
    The University of Auckland Library

    Natrual products have long been regarded as 'nature's medicine chest' because they offer a rich source of compounds with complex and novel structures tha inspire the development of new drugs. The synthesis of these challenging, naturally occurring compunds in the laboratory is a scientific endeauvour that forms the backbone of the pharmaceutical industry. ...

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  • 2-Trimethylsilyloxyfuran, CAS No: 61550-02- Update

    Brimble, Margaret; Sperry, Jonathan (2008)

    Book item
    The University of Auckland Library

    InChI = 1S/C7H12O2Si/c1-10(2,3)9-7-5-4-6-8-7/h4-6H,1-3H3 InChIKey = ILBCDLOQMRDXLN-UHFFFAOYSA-N (provides 5-substituted 2(5H)-furanones by alkylation,2 aldolization,3 and conjugate addition;4 transforms quinones into furo[3,2-b]benzofurans;5 useful for the four-carbon elongation of sugars6) Alternate Name: TMSOF. Physical Data: bp 44???46 ??C/17 mmHg; d 0.93 g mL???1. Solubility: sol most organic solvents, e.g. CH2Cl2, Et2O, benzene, THF, MeCN. Form Supplied in: colorless liquid; commercially available (98% pure) but expensive. Preparative Method: accessible by silylation of 2(5H)-furanone,1c,5b which is obtained at very low cost by oxidation of furfural (see also ). Handling, Storage, and Precautions: flammable liquid; sensitive to moisture. To avoid hydrolysis, it should be kept under Ar at ???18 ??C or below. For best results, reactions should be performed under strictly anhydrous conditions in aprotic solvents. Use in a fume hood.

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  • Synthesis of mannosylated glycopeptides as components for synthetic vaccines

    Kowalczyk, R; Brimble, Margaret; Dunbar, R (2009)

    Book item
    The University of Auckland Library

    Introduction The immune system often recognizes tumour cells and infectious agents from the unique peptides (epitopes) found on their surfaces [1] therefore, synthetic vaccines that combine many epitopes together with appropriate glycal adjuvants that stimulate Cytotoxic T Lymphocytes (CTLs) would have considerable clinical utility. The cells responsible for initiating an immune response are APCs (antigenpresenting cells) that capture and process antigen-derived peptides for presentation to CTLs. Dendritic cells are a type of APC that express receptors capable of recognizing and internalizing foreign agents. Several of these receptors are C-type lectin receptors that bind carbohydrates [2]. The receptors we are interested in, in particular, are mannose receptors that are known in the uptake and presentation of mannosylated antigens to T cells [3]. In order to target these receptors and test their specificity for binding human skin APCs in vitro we have synthesized twenty mannosylated peptide derivatives, which differ in their chain length and the position of the mannosyl unit on the peptide backbone.

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  • GPE Analogs and Peptidomimetics

    Abood, NA; Brimble, Margaret (2003-03-20)

    Patent
    The University of Auckland Library

    This invention relates to analogs and peptidomimetics of glycyl-L-prolyl-L-glutamic acid (GPE). In particular, this invention relates to GPE analogs and peptidomimetics that are anti-apoptotic and anti-necrotic, to methods of making them, to pharmaceutical compositions containing them, and to their use.

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  • A synthetic study towards aryl 6,6-spiroacetal analogues of rubromycin

    Choi, Peter; Rathwell, DC; Brimble, Margaret (2008)

    Conference poster
    The University of Auckland Library

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  • Treatment of non-convulsive seizures in brain injury using G-2-methyl-prolyl glutamate

    Gluckman, Peter; Brimble, Margaret; Wilson, D; Tortella, FC; Williams, AJ; Xi-Chun, ML; Hartings, JA; Gryder, D (2010-05-11)

    Patent
    The University of Auckland Library

    Aspects of this invention include the use of G-2MePE to treat patients with brain injury characterized by non-convulsive seizures. G-2MePE is useful in treating brain injuries caused by traumatic brain injury, stroke, hypoxia/ischemia and toxic injury.

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  • Pyrans and their Benzo Derivatives: Synthesis

    Brimble, Margaret; Sperry, Jonathan; Gibson, JS (2008)

    Book item
    The University of Auckland Library

    The abundance of six-membered oxygen containing heterocycles in bioactive natural products continues to encourage the development of new and improved syntheses. There is a vast amount of new literature dedicated to the synthesis of pyrans and their benzo derivatives; however, many traditional approaches are still of great value and this chapter should be read in conjunction with the corresponding chapters in the first and second editions of Comprehensive Heterocyclic Chemistry ....

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  • Di-(-)-(1R,2S)-2-phenyl-1-cyclohexyl Diazenedicarboxylate

    Brimble, Margaret (2002)

    Book item
    The University of Auckland Library

    InChI = 1S/C26H30N2O4/c29-25(31-23-17-9-7-15-21(23)19-11-3-1-4-12-19)27-28-26(30)32-24-18-10-8-16-22(24)20-13-5-2-6-14-20/h1-6,11-14,21-24H,7-10,15-18H2/b28-27+/t21-,22-,23+,24+/m0/s1 InChIKey = RHBWBKFUCXVAMA-KQEKZTIUSA-N (reagent used as a chiral azo-enophile in asymmetric azo-ene reactions) Alternate Name: (1R-{1??[E(1R*,2S*)],2??})-Bis(2-phenylcyclohexyl) diazenedicarboxylate. Physical Data: [??]D ???56.9 (c 0.65, CHCl3). Solubility: soluble in CH2Cl2, diethyl ether, and most organic solvents. Form Supplied in: yellow oil. Analysis of Reagent Purity: 1H NMR, IR, TLC, elemental analysis. Preparative Methods: The title reagent is prepared1 by reaction of (1R, 2S)-2-phenyl-1-cyclohexanol with excess phosgene in the presence of quinoline to afford a chloroformate which is treated directly with hydrazine monohydrate (0.5 equiv) to afford di-(???)-(1R, 2S)-2-phenyl-1-cyclohexyl diazanedicarboxylate. Oxidation of the diazanedicarboxylate to the diazenedicarboxylate is then readily effected using N-bromosuccinimide and pyridine (eq 1).

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  • Professor Jim Coxon. A Tribute

    Brimble, Margaret; Steel, P (2006)

    Journal article
    The University of Auckland Library

    This special issue of the ARKIVOC is dedicated to Professor Jim Coxon to mark his 65 th birthday and acknowledge his contribution to New Zealand science through his diverse achievements in mechanistic organic chemistry carried out at the University of Canterbury.

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  • The enantioselective synthesis of tetracyclic methyllycaconitine analogues

    Sparrow, K; Barker, David; Brimble, Margaret (2011)

    Journal article
    The University of Auckland Library

    A new enantioselective synthesis of ABEF ring analogues of methyllycaconitine has been developed using a chiral cobalt(III) salen-catalyzed Diels???Alder reaction to form the B ring. Subsequent elaboration to form the A, E and F rings was achieved by sequential Dieckmann, Mannich and Wacker-type cyclizations to afford tetracyclic analogues in 97.5% ee.

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  • Synthesis of a Dimeric Pyranonaphthoquinone via a Novel Double Furofuran Annulation Strategy

    Brimble, Margaret; Neville, D; Duncalf, Letecia (1998)

    Journal article
    The University of Auckland Library

    The first synthesis of a dimeric pyranonaphthoquinone 16 which is related to the naturally occurring dimeric pyranonaphthoquinones, e.g. actinorhodin 1 and crisamycin 3, is described. The key biaryl 8 is prepared by means of a Suzuki coupling reaction, utilizing the Miyaura reagent to generate the organoboron coupling partner. The first example of a double annulation of a bisquinone with 2-trimethylsilyloxyfuran to afford a bisfuronaphthofuran and subsequent double oxidative rearrangement to a dimeric pyranonaphthoquinone is described.

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  • Synthesis of a Functionalized Bis-Spiroacetal

    Brimble, Margaret; Williams, GM; Baker, R; James, M (1990)

    Journal article
    The University of Auckland Library

    The synthesis of bis-spiroacetal (15) bearing an hydroxymethyl group at C-2 is described establishing a methodology for preparation of the polyether antibiotics salinomycin and narasin. Formation of an important iodohydrin intermediate has been accomplished by a highly efficient reaction of an epoxide with LiI catalysed by BF3.Et2O in THF. Displacement of the resulting neopentyl iodide was achieved in high yield by reaction of the iodide with potassium superoxide in dimethylsulphoxide/tetrahydrofuran in the presence of 18-crown-6. The synthesis of bis-spiroacetal (15) has been achieved the following sequence.

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  • Synthesis of a New Spiroacetal Based Herbicide

    Brimble, Margaret; Johnston, Andrew; Furneaux, RH (1997)

    Journal article
    The University of Auckland Library

    [3R???, 5S???, 6S???]-3-Benzyloxy-5-methoxy-1,7-dioxaspiro[5.5]undecane 3 and [3R???, 5S???, 6S???]-3-methoxy-5-benzyloxy-1,7-dioxaspiro[5.5]undecane 4 were prepared making use of a base induced rearrangement of a 4,5-epoxy-1,7-dioxaspiro[5.5]undecane.

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  • SYNTHESIS OF A PYRANONAPHTHOQUINONE-SPIROACETAL

    Brimble, Margaret; NAIRN, M (1992-03)

    Journal article
    The University of Auckland Library

    A synthesis of pyranonaphthoquinone-spiroacetal 12 is reported which represents an efficient entry to the pentacyclic framework of the pyranonaphthoquinone antibiotic griseusin A. The key step involves assembly of the furo[3,2-b]naphtho[2,3-d]pyran 11via a ceric ammonium nitrate oxidative rearrangement of the furo[3,2-b]naptho[2,1-d]furan 10. This latter heterocycle 10 in turn was constructed via the uncatalysed 1,4-addition of 2-trimethylsilyloxyfuran 9 to naphthoquinone 8. Naphthoquinone 8 is readily available from 1,4-dimethoxynaphthalene-2-carbaldehyde 3 and acetylene 4.

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  • A Convergent Synthesis of the [4.4]-Spiroacetal-gamma-lactones Cephalosporolides E and F

    Brimble, Margaret; Finch, OC; Heapy, AM; Fraser, JD; Furkert, DP; O'Connor, PD (2011)

    Journal article
    The University of Auckland Library

    A short convergent synthesis of the fungal metabolites cephalosporolides E and F is reported. The key step makes use of a chelation-controlled Mukaiyam

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  • Synthesis of the Bis-Spiroacetal Moiety of 17-epi-20-Deoxysalinomycin

    Brimble, Margaret; Williams, GM (1992)

    Journal article
    The University of Auckland Library

    The synthesis of the bis-spiroacetal moiety of 17-epi-20-deoxysalinomycin (4) is reported in which the key step involves oxidative cyclization of the hydroxy spiroacetals 14 and 15 to the bis-spiroacetals 16 and 17 using (diacetoxyiodo)benzene and iodine under photolytic conditions.

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  • SYNTHESIS OF THE INSECT FEEDING DETERRENT PERAMINE VIA MICHAEL ADDITION OF A PYRROLE ANION TO A NITROALKENE

    Brimble, Margaret; ROWAN, DD (1990-02-01)

    Journal article
    The University of Auckland Library

    A total synthesis of peramine (1), the major insect feeding deterrent isolated from perennial ryegrass (Lolium perenne L.) infected with the endophytic fungus Acremonium lolii is reported. The key step involves the Michael addition of the potassium salt of methyl pyrrole-2-carboxylate (3) to the nitroalkene (4) providing access to a 3-substituted pyrrolo[1,2-a]pyrazin-1 (2H)-one (10). Displacement of the allylic bromide (11) by cyanomethyl cuprate provided the methodology for introducing the desired monosubstituted guanidino group via the nitrite (12).

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