James McNulty

Summary

Affiliation: McMaster University
Country: Canada

Publications

  1. ncbi request reprint Efficient carbonylation reactions in phosphonium salt ionic liquids: anionic effects
    James McNulty
    Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1, Canada
    Org Lett 9:4575-8. 2007
  2. doi request reprint Rapid and efficient entry to vinyl silanes from aldehydes employing a novel metalation-Peterson sequence
    James McNulty
    Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario, Canada
    Chem Commun (Camb) . 2008
  3. ncbi request reprint Scope and mechanistic insights into the use of tetradecyl(trihexyl)phosphonium bistriflimide: a remarkably selective ionic liquid solvent for substitution reactions
    James McNulty
    Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1, Canada
    Chemistry 12:9314-22. 2006
  4. doi request reprint Enol ethers as carbonyl surrogates in a modification of the Povarov synthesis of 3-aryl quinolines and their anti-Toxoplasma activity
    Carla E Brown
    Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, Canada L8S 4M1
    Org Biomol Chem 14:5951-5. 2016
  5. ncbi request reprint Regiocontrol in the oxidative radical fragmentation of benzilidene acetals and its mechanistic implications
    James McNulty
    Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario, Canada L8S 4M1
    J Org Chem 69:563-5. 2004
  6. doi request reprint Synthesis of the cyanobacterial metabolite nostodione A, structural studies and potent antiparasitic activity against Toxoplasma gondii
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, CanadaL8S 4M1
    Org Biomol Chem 13:10015-24. 2015
  7. doi request reprint Enantioselective organocatalytic Michael/aldol sequence: anticancer natural product (+)-trans-dihydrolycoricidine
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1 Canada www chemistry mcmaster ca mcnulty index html
    Angew Chem Int Ed Engl 53:8450-4. 2014
  8. doi request reprint Total synthesis of the cyanobacterial metabolite nostodione A: discovery of its antiparasitic activity against Toxoplasma gondii
    J McNulty
    Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, Canada L8S 4M1
    Chem Commun (Camb) 50:8904-7. 2014
  9. doi request reprint Investigation of aryl halides as ketone bioisosteres: refinement of potent and selective inhibitors of human cytochrome P450 19A1 (aromatase)
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ont L8S 4M1, Canada Electronic address
    Bioorg Med Chem Lett 23:6060-3. 2013
  10. doi request reprint Synthesis and anti-toxoplasmosis activity of 4-arylquinoline-2-carboxylate derivatives
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, Canada L8S 4M1
    Org Biomol Chem 12:255-60. 2014

Collaborators

Detail Information

Publications45

  1. ncbi request reprint Efficient carbonylation reactions in phosphonium salt ionic liquids: anionic effects
    James McNulty
    Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1, Canada
    Org Lett 9:4575-8. 2007
    ..Solvent-free product isolation and recycling of the ionic liquid containing active Pd-catalyst are also demonstrated...
  2. doi request reprint Rapid and efficient entry to vinyl silanes from aldehydes employing a novel metalation-Peterson sequence
    James McNulty
    Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario, Canada
    Chem Commun (Camb) . 2008
    ....
  3. ncbi request reprint Scope and mechanistic insights into the use of tetradecyl(trihexyl)phosphonium bistriflimide: a remarkably selective ionic liquid solvent for substitution reactions
    James McNulty
    Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1, Canada
    Chemistry 12:9314-22. 2006
    ..The lack of any basic entity in the phosphonium bistriflimide ionic liquid appears to prevent any potential base-mediated elimination reactions, which makes this a highly selective medium for use in general substitution reactions...
  4. doi request reprint Enol ethers as carbonyl surrogates in a modification of the Povarov synthesis of 3-aryl quinolines and their anti-Toxoplasma activity
    Carla E Brown
    Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, Canada L8S 4M1
    Org Biomol Chem 14:5951-5. 2016
    ....
  5. ncbi request reprint Regiocontrol in the oxidative radical fragmentation of benzilidene acetals and its mechanistic implications
    James McNulty
    Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario, Canada L8S 4M1
    J Org Chem 69:563-5. 2004
    ..Reversed regiospecificity in the fragmentation is demonstrated for the first time through the incorporation of an allylic alcohol into the benzilidene acetal...
  6. doi request reprint Synthesis of the cyanobacterial metabolite nostodione A, structural studies and potent antiparasitic activity against Toxoplasma gondii
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, CanadaL8S 4M1
    Org Biomol Chem 13:10015-24. 2015
    ..The first single crystal X-ray structural determination on a member of this series is reported along with SAR studies identifying potent inhibitors of invasion and replication of the parasitic protozoan Toxoplasma gondii. ..
  7. doi request reprint Enantioselective organocatalytic Michael/aldol sequence: anticancer natural product (+)-trans-dihydrolycoricidine
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1 Canada www chemistry mcmaster ca mcnulty index html
    Angew Chem Int Ed Engl 53:8450-4. 2014
    ..The sequence results in the formation of an advanced intermediate, containing three stereogenic centers, in one step which and was converted into the title compound in eight steps. ..
  8. doi request reprint Total synthesis of the cyanobacterial metabolite nostodione A: discovery of its antiparasitic activity against Toxoplasma gondii
    J McNulty
    Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, Canada L8S 4M1
    Chem Commun (Camb) 50:8904-7. 2014
    ..A small assemblage of structural analogues were prepared and their cytotoxicity and anti-invasion activity against the protozoal parasite Toxoplasma gondii is reported for the first time. ..
  9. doi request reprint Investigation of aryl halides as ketone bioisosteres: refinement of potent and selective inhibitors of human cytochrome P450 19A1 (aromatase)
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ont L8S 4M1, Canada Electronic address
    Bioorg Med Chem Lett 23:6060-3. 2013
    ..Structure-activity data generated from both syn- and anti-aldol precursors provides significant insights into the requirements for enhanced potency, validating this novel ketone-to-aryl halide bioisostere hypothesis. ..
  10. doi request reprint Synthesis and anti-toxoplasmosis activity of 4-arylquinoline-2-carboxylate derivatives
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, Canada L8S 4M1
    Org Biomol Chem 12:255-60. 2014
    ..Mechanistic insights into the role of Lewis acid (silver triflate) versus Bronsted acid (triflic acid) catalysis are revealed clarifying aspects of the mechanism of the quinoline synthesis. ..
  11. doi request reprint Phthalide: a direct building-block towards P,O and P,N hemilabile ligands. Application in the palladium-catalysed Suzuki-Miyaura cross-coupling of aryl chlorides
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, CanadaL8S 4M1
    Org Biomol Chem 11:2404-7. 2013
    ..Pd-complexes of one such ligand were found highly effective in general Suzuki-Miyaura cross-coupling reactions, including deactivated and hindered aryl chlorides...
  12. doi request reprint Amine- and sulfonamide-promoted Wittig olefination reactions in water
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, Hamilton, ON, Canada
    Chemistry 17:8794-8. 2011
    ..Possible catalytic cycles involving imines and iminium intermediates are discussed...
  13. doi request reprint Discovery of a novel class of aldol-derived 1,2,3-triazoles: potent and selective inhibitors of human cytochrome P450 19A1 (aromatase)
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ont, Canada L8S 4M1
    Bioorg Med Chem Lett 22:718-22. 2012
    ..Structure-activity data generated from both syn- and anti-aldol adducts provides initial insights into the requirements for both potency and selectivity...
  14. doi request reprint Structure-activity studies on the lycorine pharmacophore: A potent inducer of apoptosis in human leukemia cells
    James McNulty
    Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario, Canada L8S 4M1
    Phytochemistry 70:913-9. 2009
    ..Further insights into the nature of this interesting apoptosis-inducing pharmacophore are described, including the requirement of both free hydroxyl groups in ring-C...
  15. doi request reprint Human cytochrome P450 liability studies of trans-dihydronarciclasine: a readily available, potent, and selective cancer cell growth inhibitor
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario, Canada, L8S 4M1
    J Nat Prod 74:106-8. 2011
    ..This study elevates the status of trans-dihydronarciclasine (5) as a highly privileged, readily available molecule, with potent and selective anticancer activity...
  16. doi request reprint The First Well-Defined Silver(I)-Complex-Catalyzed Cycloaddition of Azides onto Terminal Alkynes at Room Temperature
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1 Canada, Fax 1 905 522 2509
    Chemistry 17:14727-30. 2011
    ..The synthesis of a stable, well-defined Ag(I) complex of type [Ag(I) (L(2) )(OAc)] is described, along with the unprecedented ability of this complex to promote the general Ag-AAC at room temperature...
  17. ncbi request reprint Cytochrome P450 3A4 inhibitory activity studies within the lycorine series of alkaloids
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario L8S 4M1, Canada
    Nat Prod Commun 5:1195-200. 2010
    ....
  18. doi request reprint Structure-activity studies on acetylcholinesterase inhibition in the lycorine series of Amaryllidaceae alkaloids
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, Canada
    Bioorg Med Chem Lett 20:5290-4. 2010
    ..Important elements of this novel pharmacophore were elucidated through structure-activity relationship (SAR) studies...
  19. ncbi request reprint A synthesis of 3-deoxydihydrolycoricidine: refinement of a structurally minimum pancratistatin pharmacophore
    James McNulty
    Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ont, Canada L8S 4M1
    Bioorg Med Chem Lett 15:5315-8. 2005
    ..In addition to those features previously identified, the requirement of a 2,3,4-triol functionalized ring-C is now definitely established as the minimum pharmacophoric element for potent anticancer activity...
  20. doi request reprint Potent and selective inhibition of human cytochrome P450 3A4 by seco-pancratistatin structural analogs
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ont, Canada L8S 4M1
    Bioorg Med Chem Lett 20:2335-9. 2010
    ....
  21. doi request reprint Isolation of flavonoids from the heartwood and resin of Prunus avium and some preliminary biological investigations
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, ON, Canada L8S 4M1
    Phytochemistry 70:2040-6. 2009
    ..The defensive role of these natural plant flavonoids as antifungal phytoalexins and phytoanticipins is discussed...
  22. doi request reprint Structure-activity studies on seco-pancratistatin analogs: potent inhibitors of human cytochrome P450 3A4
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ont, Canada L8S 4M1
    Bioorg Med Chem Lett 19:5607-12. 2009
    ..These studies identify potential roadblocks and will guide the further development of a viable selective clinical pancratistatin derivative...
  23. ncbi request reprint Structure activity studies on the crinane alkaloid apoptosis-inducing pharmacophore
    James McNulty
    Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1, Canada
    Nat Prod Commun 4:483-8. 2009
    ....
  24. doi request reprint Selective cytochrome P450 3A4 inhibitory activity of Amaryllidaceae alkaloids
    James McNulty
    Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ont, Canada L8S 4M1
    Bioorg Med Chem Lett 19:3233-7. 2009
    ..Important pharmacological features uncovered include the lack of CYP3A4 inhibitory activity seen for galanthamine and the selective activity that is seen with narciclasine over pancratistatin...
  25. ncbi request reprint Discovery of the apoptosis-inducing activity and high accumulation of the butenolides, menisdaurilide and aquilegiolide in Dicentra spectabilis
    James McNulty
    Department of Chemistry, McMaster University, Hamilton, Ontario, Canada
    Planta Med 73:1543-47. 2007
    ..The high abundance and apoptosis-inducing activity reported here indicates that these constituents play a more significant role than the hormonal action previously attributed to them...
  26. doi request reprint synthesis and biological evaluation of fully functionalized seco-pancratistatin analogues
    James McNulty
    Department of Chemistry, McMaster University, Hamilton, Ontario, Canada
    J Nat Prod 71:357-63. 2008
    ..The B,C- seco compounds 25 and 26 exhibited low activity (ED 50 > 30 microg/mL) for inducing apoptosis in human cancer cells...
  27. ncbi request reprint Selective apoptosis-inducing activity of crinum-type Amaryllidaceae alkaloids
    James McNulty
    Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ont, Canada L8S 4M1
    Phytochemistry 68:1068-74. 2007
    ..Structure-activity relationships demonstrated the requirement for both an alpha-C2 bridge and a free hydroxyl at the C-11 position as pharmacophoric requirements for this activity...
  28. doi request reprint A novel synthetic C-1 analogue of 7-deoxypancratistatin induces apoptosis in p53 positive and negative human colorectal cancer cells by targeting the mitochondria: enhancement of activity by tamoxifen
    Dennis Ma
    Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Avenue, Windsor, ON, N9B 3P4, Canada
    Invest New Drugs 30:1012-27. 2012
    ..Hence, JCTH-4 is a novel compound capable of selectively inducing apoptosis and autophagy in CRC cells alone and in combination with TAM and may serve as a safer and more effective alternative to current cancer therapies...
  29. ncbi request reprint Synergy of Pancratistatin and Tamoxifen on breast cancer cells in inducing apoptosis by targeting mitochondria
    Peter Siedlakowski
    Department of Chemistry and Biochemistry, University of Windsor, Windsor, Ontario, Canada
    Cancer Biol Ther 7:376-84. 2008
    ....
  30. ncbi request reprint Induction of apoptotic cell death specifically in rat and human cancer cells by pancratistatin
    Siyaram Pandey
    Department of Chemistry and Biochemistry, University of Windsor, Windsor, Ontario, Canada
    Artif Cells Blood Substit Immobil Biotechnol 33:279-95. 2005
    ..The objective in the present study was to elucidate the mechanism of the anti-neoplastic action of pancratistatin and evaluate the specificity of this compound for cancer cells...
  31. doi request reprint A sol-gel-derived acetylcholinesterase microarray for nanovolume small-molecule screening
    Maria Rowena N Monton
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main St W, Hamilton, Ontario L8S 4M1, Canada
    Anal Chem 82:9365-73. 2010
    ..IC(50) values were obtained on microarrays for compounds showing significant inhibitory activity, demonstrating the utility of arrays for quantitative inhibition assays...
  32. ncbi request reprint Suzuki cross-coupling reactions of aryl halides in phosphonium salt ionic liquid under mild conditions
    James McNulty
    Institute of Molecular Catalysis, Department of Chemistry, Brock University, St Catharines, Ontario L2S 3A1, Canada
    Chem Commun (Camb) . 2002
    ..The Suzuki cross-coupling of aryl boronic acids with aryl halides, including aryl chlorides, proceeds in the phosphonium salt ionic liquid tetradecyltrihexylphosphonium chloride under mild conditions...
  33. doi request reprint Discovery of a new class of cinnamyl-triazole as potent and selective inhibitors of aromatase (cytochrome P450 19A1)
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ont L8S 4M1, Canada
    Bioorg Med Chem Lett 24:4586-9. 2014
    ..Structure-activity data generated provides insights into the requirements for potency particularly the inclusion of an aryl bromide or chloride residue as a keto-bioisostere. ..
  34. pmc iPSC Neuronal Assay Identifies Amaryllidaceae Pharmacophore with Multiple Effects against Herpesvirus Infections
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street, West Hamilton, Ontario L8S 4M1, Canada
    ACS Med Chem Lett 7:46-50. 2016
    ..A configurationally defined (3R)-secondary alcohol at C3 proved crucial for efficacious inhibition of lytic HSV-1 infection. ..
  35. pmc Selective cytotoxicity of pancratistatin-related natural Amaryllidaceae alkaloids: evaluation of the activity of two new compounds
    Carly Griffin
    Department of Chemistry and Biochemistry, University of Windsor, Windsor, Ontario, Canada
    Cancer Cell Int 7:10. 2007
    ..Both of these compounds lack the polyhydroxylated lycorane element of PST instead having a methoxy-substituted crinane skeleton...
  36. ncbi request reprint One step entry to P,O- and P,N-type heterocyclic tertiary phosphine ligands and application in Suzuki-Miyaura cross-coupling reactions
    Ehsan Ullah
    Department of Chemistry, McMaster University, Hamilton, Ontario, Canada L8S 4M1
    Org Biomol Chem 9:4421-4. 2011
    ..Palladium complexes of the P,N-ligand were determined to be highly active in the Suzuki-Miyaura cross-coupling reactions, including deactivated aryl chlorides...
  37. pmc DualPhos: a versatile, chemoselective reagent for two-carbon aldehyde to latent (E)-alkenal homologation and application in the total synthesis of phomolide G
    David McLeod
    Department of Chemistry and Chemical Biology, McMaster University Faculty of Science, Hamilton, Ontario, Canada L8S 4M1
    R Soc Open Sci 3:160374. 2016
    ..The strategy allows isolation of the latent alkenal intermediates or direct hydrolysis to (E)-alkenals. The robust chemical stability of the latent alkenals is demonstrated in a total synthesis of the macrolactone phomolide G...
  38. doi request reprint Asymmetric Organocatalytic Stepwise [2+2] Entry to Tetra-Substituted Heterodimeric and Homochiral Cyclobutanes
    Alex J Nielsen
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ontario, L8S 4M1, Canada
    Chemistry 22:9111-5. 2016
    ..A series of selective synthetic interconversions in these sensitive cycloadducts is also described. ..
  39. ncbi request reprint Antimitotic activity of structurally simplified biaryl analogs of the anticancer agents colchicine and combretastatin A4
    James McNulty
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main Street West, Hamilton, Ont L8S 4M1, Canada
    Bioorg Med Chem Lett 25:117-21. 2015
    ..The compounds were shown to initiate apoptosis selectively via a mechanism involving inhibition of tubulin polymerization...
  40. doi request reprint Sensitization of human melanoma cells by tamoxifen to apoptosis induction by pancratistatin, a nongenotoxic natural compound
    Sudipa June Chatterjee
    aDepartment of Chemistry and Biochemistry, University of Windsor, Windsor bDepartment of Chemistry, McMaster University, Hamilton, Ontario, Canada
    Melanoma Res 21:1-11. 2011
    ..In conclusion, combination of two nongenotoxic compounds offers a novel treatment regime for this notoriously resilient form of skin cancer. ..
  41. doi request reprint High yielding synthesis of carboranes under mild reaction conditions using a homogeneous silver(I) catalyst: direct evidence of a bimetallic intermediate
    Mohamed E El-Zaria
    Department of Chemistry and Chemical Biology, McMaster University, 1280 Main St W, Hamilton, Ont, L8S 4M1 Canada Department of Chemistry, Faculty of Science, Tanta University, 31527 Tanta Egypt
    Angew Chem Int Ed Engl 53:5156-60. 2014
    ..The process is general and provides an important new synthetic strategy for the preparation of functionalized boron clusters. ..
  42. doi request reprint Palmitoyl-DL-carnitine is a multitarget inhibitor of Pseudomonas aeruginosa biofilm development
    Iwona B Wenderska
    Department of Biochemistry and Biomedical Sciences, McMaster University, 1280 Main Street W Hamilton, ON L8S4K1, Canada
    Chembiochem 12:2759-66. 2011
    ..The ability to target multiple pathways involved in biofilm formation is desirable in an inhibitor, which makes pDLC an interesting lead for antibiofilm therapies...
  43. ncbi request reprint Antineoplastic agents 491. Synthetic conversion of aaptamine to isoaaptamine, 9-demethylaaptamine, and 4-methylaaptamine
    George R Pettit
    Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, P O Box 872404, Tempe, Arizona 85287 2404, USA
    J Org Chem 69:2251-6. 2004
    ..Evaluation as inhibitors of the PKC signal transduction pathway and against a selection of microorganisms was also undertaken. Aaptamine derivatives 3 and 5 had broad-spectrum antimicrobial activities...
  44. ncbi request reprint Antineoplastic agents. 380. Isolation and X-ray crystal structure determination of isoaaptamine from the Republic of Singapore Hymeniacidon sp. and conversion to the phosphate prodrug hystatin 1
    George R Pettit
    Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, Tempe, Arizona 85287 2404, USA
    J Nat Prod 67:506-9. 2004
    ..Because of instability, isoaaptamine (4) was converted to a stable sodium phosphate prodrug designated hystatin 1 (7)...
  45. ncbi request reprint Pancratistatin causes early activation of caspase-3 and the flipping of phosphatidyl serine followed by rapid apoptosis specifically in human lymphoma cells
    Natasha Kekre
    Department of Chemistry and Biochemistry, University of Windsor, Windsor, ON N9B 3P4, Canada
    Cancer Chemother Pharmacol 56:29-38. 2005
    ....