ORCID Profile
0000-0002-4440-3632
Current Organisation
University of Oxford
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Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C9OB01076A
Abstract: Carboxamido tetramates derived from a bicyclic skeleton provide access to compounds with antibacterial activity.
Publisher: Elsevier BV
Date: 02-1998
Publisher: Royal Society of Chemistry (RSC)
Date: 2004
DOI: 10.1039/B404325A
Abstract: The conjugate additions of Reformatsky reagents, organocuprate reagents, and hydroxylamines to a [4.3.0]-bicyclic enelactam derived from 6-oxopipecolic acid have been investigated, and found to be efficient, proceeding with excellent exo-stereocontrol, with the exception of N-benzyl-O-benzylhydroxylamine, which gives predominantly the product of endo-addition. These adducts can be readily converted to substituted piperidinones.
Publisher: Elsevier BV
Date: 04-2004
Publisher: Georg Thieme Verlag KG
Date: 2006
Publisher: Future Science Ltd
Date: 09-2015
DOI: 10.4155/FMC.15.97
Abstract: The emergence of antimicrobial resistance has created a need for the development of novel antibacterial therapies to treat infection. Natural products that exhibit antibacterial activity offer validated starting points for library generation, and the authors report here that small molecule mimics of tetramate-containing natural products may show antibacterial activity and offer the potential for further optimization.
Publisher: Elsevier BV
Date: 02-2006
Publisher: World Scientific Pub Co Pte Lt
Date: 03-2017
DOI: 10.1142/S2251237317400056
Abstract: Functional materials are available by the post-polymerization surface modification of erse polymers in a three-step process mediated, firstly, by carbene insertion chemistry, secondly, by diazonium coupling, and thirdly by modification with a remotely tethered spiropyran unit, and these materials may be used for the reversible binding and release of Penicillin V. Surface loading densities of up to 0.19[Formula: see text]mmol/g polymer are achievable, leading to materials with higher loading densities and release behavior relative to unmodified controls, and observable antibacterial biocidal activity.
Publisher: Elsevier BV
Date: 10-1999
Publisher: Elsevier BV
Date: 1989
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8OB00187A
Abstract: The formation of densely functionalised bicyclic tetramic acids by both stereoselective reduction and Grignard displacement of a Weinreb amide gives bioactive small molecules, with antibacterial activity along with some cancer-cell line inhibitory activity.
Publisher: Elsevier BV
Date: 07-2010
Publisher: American Chemical Society (ACS)
Date: 15-11-2018
Publisher: Elsevier BV
Date: 08-1997
Publisher: Elsevier BV
Date: 05-2009
Publisher: Elsevier BV
Date: 1989
Publisher: Elsevier BV
Date: 1994
Publisher: Royal Society of Chemistry (RSC)
Date: 2023
DOI: 10.1039/D3OB00376K
Abstract: Tetramates derived from phenylserines are obtained chemoselectively and diastereoselectively, and after derivatisation as their amides, in some cases exhibit excellent antibacterial activity against Gram-positive bacteria.
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C6RA03956A
Abstract: Conductive polymers filled with carbon nanotubes have been proved to have negative permittivity but the mechanism of its strange properties has not been intensively studied.
Publisher: Royal Society of Chemistry (RSC)
Date: 1988
DOI: 10.1039/C39880000828
Publisher: Elsevier BV
Date: 1992
Publisher: Royal Society of Chemistry (RSC)
Date: 1988
DOI: 10.1039/P19880002847
Publisher: Elsevier BV
Date: 09-2022
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D1SC05542A
Abstract: A study of bicyclic tetramates modified with a bulky ester, which leads to steric hindrance of distal chelating atoms, is used as a route for the alteration of metal binding ability.
Publisher: American Chemical Society (ACS)
Date: 23-02-2015
DOI: 10.1021/JO502810B
Abstract: Epoxypyrrolidinones are available by epoxidation of carboxamide-activated bicyclic lactam substrates derived from pyroglutamate using aqueous hydrogen peroxide and tertiary amine catalysis. In the case of an activating Weinreb carboxamide, further chemoselective elaboration leads to the efficient formation of libraries of epoxyketones. Deprotection may be achieved under acidic conditions to give epoxypyroglutaminols, although the ease of this process can be ameliorated by the presence of internal hydrogen bonding. Bioassay against S. aureus and E. coli indicated that some compounds exhibit antibacterial activity. These libraries may be considered to be structural mimics of the natural products pramanicin and epolactaene. More generally, this outcome suggests that interrogation of bioactive natural products is likely to permit the identification of "privileged" structural scaffolds, providing frameworks suitable for optimization in a short series of chemical steps that may accelerate the discovery of new antibiotic chemotypes. Further optimization of such systems may permit the rapid identification of novel systems suitable for antibacterial drug development.
Publisher: Wiley
Date: 06-06-2012
Abstract: A remarkable promotion: Functional groups added onto single-wall carbon nanotubes (SWNTs) can significantly influence the activity of a noble metal for formic acid oxidation. Phenolate groups on SWNTs under alkaline conditions can double the activity of 20 % w/w Pd compared to unmodified SWNTs. This catalyst has 14 times higher activity than the commercial benchmark catalyst (10 % w/w Pd on Vulcan).
Publisher: Elsevier BV
Date: 02-1995
Publisher: American Chemical Society (ACS)
Date: 27-12-2018
Publisher: Royal Society of Chemistry (RSC)
Date: 2016
DOI: 10.1039/C5RA25253A
Abstract: A range of particulate poly(ether ketone ketone)s (PEKKs) have been synthesised by a room temperature Friedel–Crafts dispersion polymerisation.
Publisher: Beilstein Institut
Date: 22-07-2018
DOI: 10.3762/BJOC.9.224
Abstract: A chemical library of carboxamide-substituted tetramates designed by analogy with antibacterial natural products, a method for their rapid construction, and the evaluation of their antibacterial activity is reported.
Publisher: Royal Society of Chemistry (RSC)
Date: 2023
DOI: 10.1039/D3OB00594A
Abstract: Chemoselective ring closure of malonamides gives oxazolidine- or imidazolidine fused tetramates, some of which show antibacterial activity against Gram positive organism these occupy a well-defined region of chemical space.
Publisher: American Chemical Society (ACS)
Date: 03-10-2015
DOI: 10.1021/ACS.LANGMUIR.5B01644
Abstract: Polystyrene thin films were functionalized using a facile two-step chemical protocol involving carbene insertion followed by azo-coupling, permitting the introduction of a range of chemical functional groups, including aniline, hexyl, amine, carboxyl, phenyl, phosphonate diester, and ethylene glycol. X-ray photoelectron spectroscopy (XPS) confirmed the success of the two-step chemical modification with a grafting density of at least 1/10th of the typical loading density (10(14)-10(15)) of a self-assembled monolayer (SAM). In situ, real-time quartz crystal microbalance with dissipation (QCM-D) studies show that the dynamics of binding of bovine serum albumin (BSA) are different at each modified surface. Mass, viscoelastic, and kinetic data were analyzed, and compared to cheminformatic descriptors (i.e., c log P, polar surface area) typically used for drug discovery. Results show that functionalities may either resist or adsorb BSA, and uniquely influence its adsorption dynamics. It is concluded that carbene-based surface modification can usefully influence BSA binding dynamics in a manner consistent with, and more robust than, traditional systems based on SAM chemistry.
Publisher: Georg Thieme Verlag KG
Date: 19-01-2011
Publisher: Elsevier BV
Date: 04-2002
Publisher: Georg Thieme Verlag KG
Date: 03-2007
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C7OB01148B
Abstract: Fused systems are formed preferentially, under standard conditions, but spiro systems are accessible only when the formation of the fused system is blocked and with careful optimisation of reaction conditions.
Publisher: Elsevier BV
Date: 02-2002
Publisher: Wiley
Date: 19-06-2018
Abstract: Two bis(diaryldiazomethane)s substituted with amino groups are synthesized and used for the surface modification of membranes electrospun from gelatin. These membranes are then reacted with tolylene-2,4-diisocyanate to give urea-functionalized materials, so that hydrogen peroxide can be reversibly bound onto their surface. These membranes are characterized by scanning electron microscopy, XPS, differential scanning calorimeter, and tensile test to show their surface properties and bulk properties. The surface modification with amino-substituted diazomethanes and the subsequent cross-linking reaction with diisocyanates contribute to high loadings of hydrogen peroxide, and greatly increase the antibacterial activity of gelatin-derived membranes, which open a new horizon in the preparation of high loading antiseptic/antibacterial biomacromolecular surfaces and interfaces.
Publisher: Elsevier BV
Date: 08-2022
Publisher: American Chemical Society (ACS)
Date: 11-1988
Publisher: MDPI AG
Date: 23-11-2015
DOI: 10.3390/M875
Publisher: Royal Society of Chemistry (RSC)
Date: 2000
DOI: 10.1039/B001999M
Publisher: Elsevier BV
Date: 03-1992
Publisher: Elsevier BV
Date: 08-1994
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C6OB02828D
Abstract: Mono and dihydroxypyrrolidinones are readily available by direct oxygenation of a pyroglutamate-derived bicyclic lactam with high diastereoselectivity, and these may be manipulated further in protected or unprotected form by Grignard addition to a pendant Weinreb amide to give acylhydroxypyrrolidinones.
Publisher: Elsevier BV
Date: 07-2008
DOI: 10.1016/J.BMCL.2008.05.105
Abstract: Structural analysis of oxazolomycin and simpler fragments containing a common 3-hydroxy-2,2-dimethylpropanamide moiety has indicated that a U-shaped conformation is preferred, in some cases stabilised by hydrogen bonding between the N-H and O-H residues, as shown by a combination of molecular modelling, NMR spectroscopic and single crystal X-ray analysis. A direct synthesis of this unit has been established via the opening of beta-lactones by a range of amines, and their antibacterial activity been shown to vary with the hydrophobic character of the substituents.
Publisher: Royal Society of Chemistry (RSC)
Date: 2003
DOI: 10.1039/B303924B
Abstract: Alkylation reactions using alpha-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.
Publisher: Elsevier BV
Date: 1989
Publisher: MDPI AG
Date: 13-01-2017
Publisher: Elsevier BV
Date: 04-2020
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2OB26423D
Abstract: Substituted pyrrolines are available by ring closure initiated by direct nucleophilic attack of stabilized enolates at the nitrogen of oximes activated with a leaving group, in a process which effectively out-competes the more usual Beckmann rearrangement. Subsequent reduction provides diastereoselective access to the corresponding pyrrolidines. This provides a rapid route to saturated heterocyclic systems from readily available precursors.
Publisher: Informa UK Limited
Date: 04-2005
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C1JM13783B
Publisher: Elsevier BV
Date: 04-2013
Publisher: Wiley
Date: 18-05-2014
Abstract: Inspired by the core fragment of antibacterial natural products such as streptolydigin, 3-acyltetramic acids and 3-acylpiperidine-2,4-diones have been synthesised from the core heterocycle by direct acylation with the substituted carboxylic acids using a strategy which permits ready access to a structurally erse compound library. The antibacterial activity of these systems has been established against a panel of Gram-positive and Gram-negative bacteria, with activity mostly against the former, which in some cases is very potent. Data consistent with modes of action against undecaprenylpyrophosphate synthase (UPPS) and/or RNA polymerase (RNAP) for a small subset of the library has been obtained. The most active compounds have been shown to exhibit binding at known binding sites of streptolydigin and myxopyronin at UPPS and RNAP. These systems offer potential for their antibacterial activity, and further demonstrate the use of natural products as biologically validated starting points for drug discovery.
Publisher: Elsevier BV
Date: 03-2009
Publisher: American Chemical Society (ACS)
Date: 30-07-2010
DOI: 10.1021/LA1023482
Abstract: Functionalized diarylcarbenes are excellent reactive intermediates suitable for the direct surface modification of organic polymers, and these may be used to introduce urea and thiourea functions onto polystyrene at loading levels of up to 2.3 x 10(13) molecules/cm(2). These functions are capable of the reversible binding and release of peroxide at loading levels of up to 0.6 mmol/g and give polymers that display biocidal activity against a spectrum of gram-positive and gram-negative bacteria.
Publisher: Elsevier BV
Date: 08-1994
Publisher: American Chemical Society (ACS)
Date: 26-04-2011
DOI: 10.1021/JP201967N
Publisher: Informa UK Limited
Date: 23-09-2009
Publisher: MDPI AG
Date: 21-12-2022
DOI: 10.3390/ANTIBIOTICS12010009
Abstract: We report that phthalimides may be cyclized using a Mukaiyama-type aldol coupling to give variously substituted fused lactam (1,2,3,9b-tetrahydro-5H-pyrrolo[2,1-a]isoindol-5-one) systems. This novel process shows a high level of regioselectivity for o-substituted phthalimides, dictated by steric and electronic factors, but not for m-substituted phthalimides. The initial aldol adduct is prone to elimination, giving 2,3-dihydro-5H-pyrrolo[2,1-a]isoindol-5-ones, and the initial cyclisation can be conducted in such a way that aldol cyclisation-elimination is achievable in a one-pot approach. The 2,3-dihydro-5H-pyrrolo[2,1-a]isoindol-5-ones possess cross conjugation and steric effects which significantly influence the reactivity of several functional groups, but conditions suitable for epoxidation, ester hydrolysis and amide formation, and reduction, which provide for ring manipulation, were identified. Many of the derived lactam systems, and especially the eliminated systems, show low solubility, which compromises biological activity, although in some cases, antibacterial and cytotoxic activity was found, and this new class of small molecule provides a useful skeleton for further elaboration and study.
Publisher: Elsevier BV
Date: 10-2007
Publisher: Elsevier BV
Date: 12-2002
Publisher: Royal Society of Chemistry (RSC)
Date: 2005
DOI: 10.1039/B414856H
Abstract: A method for the application of carbenes as reactive intermediates for surface modification of polymeric substrates has been developed the efficacy of the process has been demonstrated by irreversible dyeing of polystyrene, polythene, nylon, silica, and controlled pore glass, and to a limited extent, polytetrafluoroethylene.
Publisher: Wiley
Date: 1999
DOI: 10.1002/(SICI)1096-9888(199901)34:1<60::AID-JMS764>3.0.CO;2-Q
Publisher: Royal Society of Chemistry (RSC)
Date: 02-07-2002
DOI: 10.1039/B103777N
Abstract: Recent developments in the understanding of the molecular function of memory and other CNS-mediated processes have arisen from the multidisciplinary interplay of excitatory amino acid synthesis and medicinal chemistry, X-ray crystallographic structural protein analysis, molecular biology, pharmacology and physiology. This review seeks to place recent synthetic developments of EAA analogues in the wider pharmacological setting, illustrating the need for and importance of these compounds.
Publisher: Georg Thieme Verlag KG
Date: 27-08-2009
Publisher: Elsevier BV
Date: 03-1991
Publisher: Royal Society of Chemistry (RSC)
Date: 2008
DOI: 10.1039/B811642C
Abstract: 2,2,5-Trisubstituted pyrrolidines are available from allylic pyroglutamates by Ireland-Claisen ester rearrangement followed by Eschenmoser sulfide contraction and reduction in a highly diastereoselective and efficient sequence. Some of the products from this sequence exhibit activity against S. aureus, but are much less active against E. coli.
Publisher: Elsevier BV
Date: 09-2004
Publisher: Royal Society of Chemistry (RSC)
Date: 1984
DOI: 10.1039/C39840000965
Publisher: Elsevier BV
Date: 08-1997
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2NJ00002D
Publisher: American Chemical Society (ACS)
Date: 07-12-2011
DOI: 10.1021/AC2028886
Abstract: A newly designed Pb(II) potentiometric sensor based on intrinsically conducting nanoparticles of solid poly(aniline-co-2-hydroxy-5-sulfonic aniline) possessing many ligating functional groups like -NH-, -N=, -OH, -SO(3)H, -NH(2) as ionophores in plasticizer-free vinyl resin solid membranes has been fabricated. A linear Nernstian response is obtained within a wide Pb(II) activity range from 1.0 × 10(-3) to 1.0 × 10(-10) M with a detection limit as low as 2.2 × 10(-11) M. The pH independent plateau ranges between 3.5 and 7.0. After 15 months' usage, the sensor maintains 95% performance parameters. Its anti-interference ability to Cu(II), Cd(II), Ag(I), and Hg(II) is much stronger than other sensors with a detection limit at (sub)nanomolar level. Electrochemical impedance spectroscopy reveals that the solid sensing membrane has a diffusion coefficient of around 5 × 10(-14) to 1 × 10(-13) cm(2) s(-1). The much lower diffusion coefficient for Pb(II) is highly beneficial for the elimination of Pb(II) flux across the membrane. The wide detection concentration range, low detection limit, high selectivity, extensive pH window, and long lifetime make for a robust sensor giving reliable measurement of Pb(II) content with potential application in real-world s les at trace levels.
Publisher: Wiley
Date: 18-12-2017
Publisher: Elsevier BV
Date: 07-1991
Publisher: Springer Science and Business Media LLC
Date: 24-06-1996
Publisher: Elsevier BV
Date: 1986
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C1OB05708A
Abstract: The synthesis and likely conformational structure of rigid spirocyclic bislactams and lactam-lactones derived from pyroglutamic acid, and their suitability as lead structures for applications in drug development programmes using cheminformatic analysis, has been investgated.
Publisher: Springer Science and Business Media LLC
Date: 30-10-2011
Publisher: American Chemical Society (ACS)
Date: 20-01-2011
DOI: 10.1021/JO102304Y
Abstract: The synthesis of 3-acyltetramic acids, the substructure of bioactive natural products, via O-acylation of tetramic acids with carboxylic acids followed by acyl migration, has been investigated. This acylation sequence is mediated by N,N'-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) and is very sensitive to the nature of the nitrogen substituent (R(1)), the nature of the carboxylic acid (R(2)CO(2)H), and the amount of DMAP. Acylation of N-acyl tetramic acids with an alkyl carboxylic acid using 1.3 equiv of DMAP (with 1.1 equiv of DCC) unexpectedly gave the 3-acyltetramic acid directly as a result of acyl migration induced by excess amounts of DMAP. On the other hand, N-unsubstituted, N-alkyl, and N-acyl tetramic acids with alkyl and aromatic carboxylic acids gave the O-acyl tetramic acids by using only 0.1 equiv of DMAP (with 1.1 equiv of DCC) these could be further rearranged to the acyl product by treatment with excess DMAP. The tautomeric equilibrium of these 3-acyltetramic acids in solution was found to strongly depend on the nitrogen substituent group (R(1)) rather than the 3-acyl group.
Publisher: Elsevier BV
Date: 04-2014
DOI: 10.1016/J.BMCL.2014.03.013
Abstract: The synthesis and evaluation of 3-enaminetetramic acids as antibacterial agents is reported contrary to the analogous 3-acyltetramic acids, the enaminetetramic acid class of compound exhibits modest antibacterial activity against a limited spectrum of organisms, and even that activity is strongly dependent on the identity of the tetramate ring substituents. Moreover, these compounds appear to have a different mode of action to the analogous 3-acyltetramic acids, and appear to offer more limited opportunity for further elaboration in drug discovery.
Publisher: Royal Society of Chemistry (RSC)
Date: 2004
DOI: 10.1039/B316037H
Abstract: The synthesis and alkylation of [4.3.0]-bicyclic lactams, derived from 6-oxopipecolic acid, have been investigated. Alkylation can proceed with predominantly exo-diastereoselectivity, but the efficiency of this process depends on the substitution at the hemiaminal ether system. These products can be readily deprotected to give substituted hydroxymethyl lactams in good yield.
Publisher: No publisher found
Date: 1996
Publisher: Royal Society of Chemistry (RSC)
Date: 2005
DOI: 10.1039/B506366C
Abstract: A 1 : 1 crystalline complex of lead(IV) tetraacetate and pyridine (LTA-py) has been prepared. The single-crystal X-ray structure, at 296 and 150 K, establishes the presence of a relatively short Pb-N bond (2.307 A) within an intriguing seven-coordinate lead inner sphere consisting of the pyridine ligand and two bidentate and two monodentate acetate ligands. The pyridine occupies a surprising amount of the available coordination space and has induced a dramatic change in coordination compared to the four chelating acetate ligands found in lead tetraacetate (LTA). Thermal measurements (TGA/DSC) indicate the de-coordination of pyridine and its loss from the solid between 360 and 380 K. (207)Pb CP/MAS NMR spectroscopy also demonstrates the existence of the Pb-N bond through observation of (1)J((207)Pb,(14)N)= 63 Hz and a (207)Pb-(14)N dipolar coupling constant, of 149 Hz. The solid-state (207)Pb NMR parameters are used to give insight into the coordination environment of Pb(iv) in LTA-py. In solution, ligand exchange is rapid on chemical shift and J-coupling time scales. A (207)Pb NMR study of the titration of an LTA solution by pyridine yields a stability constant for LTA-py of K = 1.5 M(-1) and predicts it to have a (207)Pb NMR chemical shift essentially identical to that observed by CP/MAS NMR in the solid state. This correlation between the solid state and solution indicates that the seven-coordinate LTA-py structure found in the crystalline state does persist in solution, and this could further explain why the addition of pyridine has such profound effects on lead(IV) carboxylate-mediated organic reactions. Simulations of exchange-broadened line shapes of (13)C CP/MAS NMR spectra in the temperature regime above 280 K indicate local motion of the pyridine rings in the form of 180 degrees jumps (activation energy 72.5 kJ mol(-1)) these are first such ring flips reported for a coordinated pyridine ligand.
Publisher: Elsevier BV
Date: 02-2004
Publisher: Elsevier BV
Date: 1990
Publisher: American Chemical Society (ACS)
Date: 09-2021
Publisher: Elsevier BV
Date: 06-2015
Publisher: Elsevier BV
Date: 04-2011
Publisher: Bentham Science Publishers Ltd.
Date: 02-2005
Publisher: Elsevier BV
Date: 08-2009
Publisher: American Chemical Society (ACS)
Date: 09-07-2019
Abstract: A general route which provides direct access to pyroglutamates from tetramates, making use of Suzuki coupling on an enol mesylate, followed by reduction, is reported. This work permits direct scaffold hopping from tetramate to substituted pyroglutamates. Some compounds in the library showed modest antibacterial activity against Gram-positive bacteria.
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C7RA05258H
Abstract: Modification of polymer beads with a functionalized bis(arylcarbene) provides access to materials with biocidal properties.
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2OB00042C
Abstract: Biomimetic intramolecular aldol reactions on oxazolidine templates derived from serine may be used to generate densely functionalised pyroglutamates, which are simpler mimics of the right hand side of oxazolomycin. Some of the compounds from this sequence exhibit in vivo activity against S. aureus and E. coli, suggesting that pyroglutamate scaffolds may be useful templates for the development of novel antibacterials, and cheminformatic analysis has been used to provide some structure-activity data.
Publisher: MDPI AG
Date: 20-02-2015
Publisher: Royal Society of Chemistry (RSC)
Date: 2003
DOI: 10.1039/B303789D
Abstract: A direct and versatile route enabling the regio- and diastereoselective synthesis of 2,5-disubstituted pyrrolidines by reduction of enamines derived from pyroglutamic acid is reported.
Publisher: Elsevier BV
Date: 09-1996
Publisher: Royal Society of Chemistry (RSC)
Date: 2012
DOI: 10.1039/C2JM34942F
Publisher: American Chemical Society (ACS)
Date: 03-09-2020
Publisher: Wiley
Date: 24-04-2013
DOI: 10.1111/CBDD.12110
Abstract: Chemoselective Dieckmann cyclization reactions may be used on oxazolidine and thiazolidine templates derived from various aldehydes to access bicyclic tetramates, which have potential as templates for chemical library construction. Bioassay against Staphylococcus aureus and Escherichia coli showed that these systems have little or no intrinsic antibacterial bioactivity.
Publisher: Elsevier BV
Date: 1987
Publisher: American Chemical Society (ACS)
Date: 05-01-2008
DOI: 10.1021/LA702701P
Abstract: A rapid route to the chemical functionalization of hydrogen-terminated diamond surfaces deposited by chemical vapor deposition involving their reaction with substituted diaryl carbenes has been investigated. To avoid difficulties in the handling of highly reactive compounds, the carbene is generated in situ from the thermal decomposition at 400 K of a thin film of the corresponding diaryl diazomethane precursor deposited at the diamond interface. X-ray photoelectron spectroscopy (XPS) has been used to verify that surface functionalization using two starting compounds, bis(4-iodophenyl) diazomethane and bis(4-nitrophenyl) diazomethane, can be achieved using this approach in agreement with recent theoretical studies. The surface grafting density is measured to be around 10(14) cm(-2) in each case. The chemistry observed is found to be insensitive to the detailed properties of the diamond film and to the presence of oxygen contamination at the hydrogen-terminated diamond surface. We further demonstrate the utility of the approach, in the case of the bound nitrophenyl compound, by its reduction to the corresponding primary amine followed by reaction with fluorescein isothiocyanate to achieve fluorescent tagging of the diamond interface.
Publisher: Elsevier BV
Date: 04-2010
DOI: 10.1016/J.BMCL.2010.02.066
Abstract: Conjugation of amide and lactam subunits by a 'Click' type approach provides access to structural mimics of the oxazolomycin series of natural products, some of which exhibit antibacterial activity.
Publisher: International Union of Crystallography (IUCr)
Date: 11-12-2004
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C4OB00095A
Abstract: An efficient approach for the introduction of 3-acyl side chain groups onto a core tetramate system, which are suitable for further manipulation by nucleophilic displacement or Horner–Wadsworth–Emmons coupling, provides access to a erse library of substituted tetramates related to two distinct classes of natural products, equisetin and pramanicin.
Publisher: Georg Thieme Verlag KG
Date: 22-03-2016
Publisher: Royal Society of Chemistry (RSC)
Date: 2023
DOI: 10.1039/D2TB02550G
Abstract: The insertion of bis(diarylcarbene)s onto a glass fiber (GF) membrane surface provided an active coating for the direct capture of protein – exemplified by the enzyme, cellulase – through a mild diazonium coupling process which does not require additional coupling agents.
Publisher: Wiley
Date: 16-06-2011
DOI: 10.1111/J.1747-0285.2011.01133.X
Abstract: Modification of the ring nucleus of tetramic acids derived from serine gives chiral heterocyclic libraries that exhibit antibacterial activity, and correlation with various physicochemical parameters indicates that chiral tetramic acids may provide a potentially valuable non-aromatic skeleton for fragment-based drug discovery.
Publisher: Royal Society of Chemistry (RSC)
Date: 2006
DOI: 10.1039/B604183C
Abstract: Methodology for the diastereoselective synthesis of 2,5-disubstituted pyrrolidines by reduction of enamines derived from pyroglutamic acid is reported the nature of nitrogen protection was found to be critical for the stereochemical control of the reaction outcome. Regioselective manipulation of the C-2 and C-5 substituents is possible, providing access to differently substituted pyrrolidines for a limited number of cases.
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C2SC21713A
Publisher: Elsevier BV
Date: 1990
Publisher: Elsevier BV
Date: 10-2008
Publisher: American Chemical Society (ACS)
Date: 20-07-2018
Abstract: Tetramic acids with unsaturated acyl chains are widely found in natural products possessing a range of biological activities, and bicyclic tetramates represent a suitable scaffold to prepare simple mimics of such complex molecules. An efficient route to functionalize the C(6)-acyl group of a bicyclic tetramate was developed and utilized to prepare a small chemical library with a range of saturated and unsaturated side-chains. The analogues with lipophilic residues possessed highly potent antibacterial activity, which was selective for Gram-positive bacteria, and the best compound was 37-fold more potent than the cephalosporin C control and with an appropriate therapeutic window.
Publisher: MDPI AG
Date: 17-07-2017
Publisher: Royal Society of Chemistry (RSC)
Date: 2003
DOI: 10.1039/B306925G
Abstract: Concise and versatile routes suitable for the synthesis of three geometric isomers of an analogue of the left hand triene sub-unit of oxazolomycin are reported. A strategy based upon a key Heck reaction was unsuccessful, and this was traced to a combination of steric encumbrance and electronic deactivation of the alkene substrate. An alternative Stille coupling strategy, however, proved to be both versatile and high yielding, and is potentially applicable to the synthesis of analogues with variation both in the side-chain geometry and in the identity of the terminal aromatic or heteroaromatic residue.
Publisher: American Chemical Society (ACS)
Date: 02-09-2022
Publisher: American Chemical Society (ACS)
Date: 05-07-2019
Abstract: Highly functionalized spirocyclic tetramates were prepared via a sequential Knoevenagel reaction and [1,5]-prototropic shift (T-reaction) of bicyclic tetramates. While these compounds isomerize in solution, stable analogues can be prepared via an appropriate choice of substituents. Further modification of these compounds allows for the introduction of aromatic groups, making them suitable as skeletons for application in medicinal chemistry.
Publisher: Elsevier BV
Date: 02-2009
Publisher: Royal Society of Chemistry (RSC)
Date: 2000
DOI: 10.1039/B002001J
Publisher: Elsevier BV
Date: 06-1996
Publisher: American Chemical Society (ACS)
Date: 25-11-2009
DOI: 10.1021/JP9081504
Publisher: Royal Society of Chemistry (RSC)
Date: 2000
DOI: 10.1039/B000432O
Publisher: Elsevier BV
Date: 2002
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C4RA01967A
Abstract: Intramolecular aldol reactions on oxazolidine templates derived from threonine may be used to generate libraries of densely functionalised pyroglutamates with a high level of diastereoselectivity.
Publisher: Wiley
Date: 03-06-2013
Publisher: Georg Thieme Verlag KG
Date: 24-08-2011
Publisher: Royal Society of Chemistry (RSC)
Date: 2006
DOI: 10.1039/B611583G
Abstract: A direct and versatile route for the reliable synthesis of trans-2,5-disubstituted pyrrolidines from pyroglutamic acid is reported, which can be conducted at scale and without chromatographic purification of key intermediates.
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C1OB05816A
Abstract: An efficient strategy for the control of the chemoselectivity in Dieckmann ring closures leading to tetramic acids derived from serine and α-methyl serine is reported, and this provides pathways to ersely substituted systems from a common starting material.
Publisher: Georg Thieme Verlag KG
Date: 08-2008
Publisher: IOP Publishing
Date: 21-08-2008
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5OB00648A
Abstract: The uncatalysed cycloaddition of substituted diaryldiazo compounds onto bicyclic unsaturated lactams derived from pyroglutamic acid efficiently leads to highly functionalised azatricyclononanes.
Publisher: Bentham Science Publishers Ltd.
Date: 10-2004
Abstract: Oxazolomycin, first isolated in 1985, is a novel bioactive compound, exhibiting potent antiviral, antibacterial and cytotoxic activity, and is now known to be the parent of a wider class of compounds. The broad-spectrum activity of oxazolomycin has been attributed to its protonophoric properties. This review outlines the isolation, structural determination, biosynthesis, bioactivity, biological mode of action and synthesis of all members of this compound class. Significantly, the oxazolomycins appear to offer not only a completely novel chemotype as a bioactive lead structure, but also a chemotype, which also exhibits an unusual biological mode of action.
Publisher: Elsevier BV
Date: 05-2018
Publisher: Royal Society of Chemistry (RSC)
Date: 1999
DOI: 10.1039/A800247I
Publisher: Walter de Gruyter GmbH
Date: 1995
Publisher: Elsevier BV
Date: 1989
Publisher: Royal Society of Chemistry (RSC)
Date: 2005
DOI: 10.1039/B503994K
Abstract: Bicyclic lactams derived from pyroglutamic acid provide a useful scaffold for synthesis of conformationally restricted analogues of lysine, ornithine and glutamine, as well as an Ala-Ala dipeptide analogue. Amino alcohol and carboxylic acid derivatives are accessible from a common intermediate. In this strategy, the bicyclic lactam system not only controls, but also facilitates the determination of the stereochemistry of the synthetic intermediates.
Publisher: Elsevier BV
Date: 03-2009
Publisher: Elsevier BV
Date: 07-2009
Publisher: Elsevier BV
Date: 1989
Publisher: Wiley
Date: 16-04-2010
Abstract: A wholly aromatic polypyrene was synthesized by direct chemical oxidative polymerization of pyrene with ferric chloride as oxidant in hexane/nitromethane. Successful synthesis of polypyrene was thoroughly confirmed by IR, UV/Vis, 1D (1)H NMR, 2D (1)H-(1)H COSY, 2D (1)H-(13)C HSQC, MALDI-TOF MS, elemental analysis, and X-ray diffraction methods. The results indicated that the polypyrene was formed mainly through dehydro coupling between 2- or 1- and 2'- or 1'-positions on pyrene rings having a degree of polymerization of around 24. The polypyrene was purified and then separated into THF-soluble (ca. 10 %) and THF-insoluble (ca. 90 %) fractions. Compared with insulating pyrene monomer, the polypyrene is a controllably conducting polymer that has low conductivity of 3.4x10(-8) S cm(-1) in its virgin state, moderate conductivity of 2.28x10(-4) S cm(-1) upon iodine doping, but much higher conductivity of up to 81.2 S cm(-1) after the insoluble polypyrene was heated up to 1300 degrees C in nitrogen with a high char yield of 70.6 %. In particular, the soluble polypyrene demonstrates much stronger visible color fluorescence and much lower toxicity than pyrene. The soluble polypyrene would be advantageous for detecting Fe(3+) with almost no interference of other metal ions. The soluble and insoluble polypyrene fractions have potential applications as intrinsically luminescent and highly conducting carbon materials, respectively.
Publisher: Elsevier BV
Date: 1991
Publisher: Elsevier BV
Date: 02-1993
Publisher: Elsevier BV
Date: 06-2010
Publisher: Elsevier BV
Date: 1994
Location: United Kingdom of Great Britain and Northern Ireland
No related grants have been discovered for Mark Moloney.