Recent Submissions

  • Synthesis of Prodigiosene-Estrogen Conjugates: optimization of protecting group strategies and anticancer properties 

    Marchal, E., Uddin, M. I., Hawco, C. L., & Thompson, A. (2015). Synthesis of prodigiosene–estrogen conjugates: optimization of protecting group strategies and anticancer properties. Canadian Journal of Chemistry, 93(5), 526-535.
    The tripyrrolic prodigiosene skeleton was conjugated to several estrogen ligands. The conjugation was achieved via an ester linker that proved to be unusually sensitive to hydrolysis during synthesis. This work describes ...
  • Regioselective Substituent Effects upon the Synthesis of Dipyrrins from 2-Formyl Pyrroles 

    Regioselective Substituent Effects upon the Synthesis of Dipyrrins from 2-Formyl Pyrroles. Beh, M.H.R.; Figliola, C.; Lund, K-l. A.R.; Kajetanowicz, A.K.; Johnsen, A.E.; Aronitz, E.M.; Thompson, A. Can. J. Chem. 2018, 96, 779-784, special issue to honour Dalhousie’s 200th anniversary (NSERC).
    The synthesis of symmetric α-free meso-H-dipyrrin hydrobromides from 5-H-2-formyl pyrroles was investigated. The self-condensation produces regioisomeric dipyrrins through the adoption of two mechanistic pathways. The key ...
  • Synthesis of symmetric meso-H dipyrrin hydrobromides from 2-formyl pyrroles 

    Lund, K. L. A., & Thompson, A. (2014). Synthesis of Symmetric meso-H-Dipyrrin Hydrobromides from 2-Formylpyrroles. Synlett, 25(08), 1142-1144. DOI: 10.1055/s-0033-1341066
    The reaction of 2-formyl pyrroles in acidic methanol gives the corresponding symmetric, meso-H 4,6-dipyrrin hydrobromides. This convenient strategy involves initial deformylation under the acidic conditions, followed by ...
  • The Use of Tin (IV) Chloride to Selectively Cleave Benzyl Esters over Benzyl Ethers and Benzyl Amines 

    Baker, A. E., Marchal, E., Lund, K. L. A., & Thompson, A. (2014). The use of tin (IV) chloride to selectively cleave benzyl esters over benzyl ethers and benzyl amines. Canadian Journal of Chemistry, 92(12), 1175-1185.
    Benzyl esters are cleaved upon reaction with SnCl4, resulting in isolation of the corresponding carboxylic acid. Importantly, benzyl ethers, amines and amides do not undergo debenzylation under these conditions, nor do a ...
  • Antimicrobial Activity of Non-natural Prodigiosenes 

    Marchal, E., Uddin, M. I., Smithen, D. A., Hawco, C. L. A., Lanteigne, M., Overy, D. P., ... & Thompson, A. (2013). Antimicrobial activity of non-natural prodigiosenes. Rsc Advances, 3(45), 22967-22971. DOI: 10.1039/c3ra45479g
    Tripyrrolic prodigiosenes, derivatives of the natural product prodigiosin, have been produced via multi-step synthesis beginning with 2-formyl pyrroles bearing various functionalities at the 4-position. Two tin complexes ...
  • Activation and Deprotection of F-BODIPYs using Boron Trihalides 

    Lundrigan, Travis, Cameron, T. Stanley, Thompson, Alison. (2014). Activation and deprotection of F-BODIPYs using boron trihalides. Chemical Communications, 50(53), 7028-7031. DOI: 10.1039/C4CC02706J
    The activation of F-BODIPYs with boron trihalides, followed by treatment with a nuclephile, effects facile substitution at boron; using water as the nucleophile promotes deprotective removal of the–BF2 moiety and thereby ...
  • Synthesis and Characterization of Pyrrolyldipyrrin F-BODIPYs 

    Greening, S. M., Robertson, K. N., & Thompson, A. (2018). Synthesis and characterization of pyrrolyldipyrrin F-BODIPYs. Photochemical & Photobiological Sciences, 17(1), 89-98. DOIO: 10.1039/C7PP00341B
    A series of synthetic analogs of the tripyrrolic natural product prodigiosin were complexed with boron trifluoride to generate the corresponding F-BODIPYs. The maximum wavelengths of absorption and emission of the ...
  • Photo-induced Anticancer Activity and Singlet Oxygen Production of Prodigiosenes 

    Savoie, H., Figliola, C., Marchal, E., Crabbe, B. W., Hallett-Tapley, G. L., Boyle, R. W., & Thompson, A. (2018). Photo-induced anticancer activity and singlet oxygen production of prodigiosenes. Photochemical & Photobiological Sciences, 17(5), 599-606. DOI: 10.1039/C8PP00060
    The photo-induced cytotoxicity of prodigiosenes is reported. One prodigiosene represents a synthetic analogue of the natural product prodigiosin, and two are conjugated to molecules that target the estrogen receptor (ER). ...
  • Synthesis and Reactivity of Aza-Dipyrrin Alkali Metal Salts 

    Synthesis and Reactivity of Aza-Dipyrrin Alkali Metal Salts. Diaz-Rodriguez, R.M.; Robertson, K.N.; Thompson, A. Chem. Commun. 2018, accepted, CC-COM-09-2018-007101.R1 (NSERC) DOI: 10.1039/C8CC07101B
    We report the lithium, sodium and potassium salts of aza-dipyrrins and detail their use as anionic aza-dipyrrinato ligand sources in complexation. Of the three types of alkali salts studied, those of lithium are found to ...
  • Use of F-BODIPYs as a protection strategy for dipyrrins: optimization of BF2 removal. 

    Smithen, D. A., Baker, A. E., Offman, M., Crawford, S. M., Cameron, T. S., & Thompson, A. (2012). Use of F-BODIPYs as a protection strategy for dipyrrins: optimization of BF2 removal. The Journal of organic chemistry, 77(7), 3439-3453. DOI: 10.1021/jo3002003
    We recently reported the first general method for the deprotection of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) involving a microwave-assisted procedure for the removal of the BF2 moiety, and liberation of ...
  • Synthesis and Antimalarial Activity of Prodigiosenes 

    Marchal, E., Smithen, D. A., Uddin, M. I., Robertson, A. W., Jakeman, D. L., Mollard, V., ... & Thompson, A. (2014). Synthesis and antimalarial activity of prodigiosenes. Organic & biomolecular chemistry, 12(24), 4132-4142. DOI:b10.1039/C3OB42548G
    Several analogues of the natural compound prodigiosin with modified A- and C-rings were synthesised as were some of their tin, cobalt, boron and zinc complexes. The antimalarial activity of these prodigiosenes was evaluated ...
  • Deuteration and Tautomeric Reactivity of the 1-Methyl Functionality of Free-base Dipyrrins 

    Groves, B. R., Cameron, T. S., & Thompson, A. (2017). Deuteration and tautomeric reactivity of the 1-methyl functionality of free-base dipyrrins. Organic & biomolecular chemistry, 15(37), 7925-7935. DOI: 10.1039/C7OB01278K
    Regioselective reactivity of the 1-methyl group of free-base dipyrrins is explored, including discussion of tautomerism to provide exocyclic alkenyl reactivity. Deuterium is installed such as to generate dipyrrins substituted ...
  • Influence of B-Ring Modifications on Proton Affinity, Transmembrane Anion Transport and Anti-Cancer Properties of Synthetic Prodigiosenes 

    Marchal, E., Rastogi, S., Thompson, A., & Davis, J. T. (2014). Influence of B-ring modifications on proton affinity, transmembrane anion transport and anti-cancer properties of synthetic prodigiosenes. Organic & biomolecular chemistry, 12(38), 7515-7522. doi: 10.1039/c4ob01399a.
    Prodigiosin is the parent compound of the tripyrrolic natural products known as the prodigiosenes. Some of these natural products and their synthetic analogs show anti-cancer, immunosuppressive and antimicrobial actions, ...
  • Decarboxylative Arylation of Substituted Pyrroles N-protected with 2-(Trimethylsilyl) ethoxymethyl (SEM) 

    Figliola, C., Greening, S. M., Lamont, C., Groves, B. R., & Thompson, A. (2018). Decarboxylative arylation of substituted pyrroles N-protected with 2-(trimethylsilyl) ethoxymethyl (SEM). Canadian Journal of Chemistry, 96(6), 534-542. doi:
    Palladium-catalyzed decarboxylative arylation is reported using pyrroles N-protected with the 2-(trimethylsilyl) ethoxymethyl (SEM) group and featuring 2-, 3- and 4-substituents about the pyrrolic framework. In contrast ...
  • Microwave-assisted reduction of F-BODIPYs and dipyrrins to generate dipyrromethanes 

    Melanson, J. A., Smithen, D. A., Cameron, T. S., & Thompson, A. (2013). Microwave-assisted reduction of F-BODIPYs and dipyrrins to generate dipyrromethanes. Canadian Journal of Chemistry, 92(8), 688-694. doi:
    The reduction of BODIPYs and dipyrrins to dipyrromethanes, via a reaction involving ethylene glycol and sodium methoxide, is reported. When benzyl alcohol is used in place of ethylene glycol, the addition of 2,4-dinitrop ...
  • Synthesis and biological evaluation of prodigiosene conjugates of porphyrin, estrone and 4-hydroxytamoxifen 

    Hawco, C. L., Marchal, E., Uddin, M. I., Baker, A. E., Corkery, D. P., Dellaire, G., & Thompson, A. (2013). Synthesis and biological evaluation of prodigiosene conjugates of porphyrin, estrone and 4-hydroxytamoxifen. Bioorganic & medicinal chemistry, 21(19), 5995-6002. DOI: 10.1016/j.bmc.2013.07.042}
    To generate the first series of prodigiosene conjugates, the tripyrrolic skeleton was appended to estrone, tamoxifen and porphyrin frameworks by way of ester linkers and various hydrocarbon chain lengths. The ability of ...
  • An Improved Method for the Synthesis of F-BODIPYs from Dipyrrins and Bis(dipyrrin)s 

    Lundrigan, T., Baker, A. E., Longobardi, L. E., Wood, T. E., Smithen, D. A., Crawford, S. M., ... & Thompson, A. (2012). An Improved Method for the Synthesis of F-BODIPYs from Dipyrrins and Bis (dipyrrin) s. Organic letters, 14(8), 2158-2161. DOI: 10.1021/ol300681w
    An improved methodology for the synthesis of F-BODIPYs from dipyrrins and bis(dipyrrin)s is reported. This strategy employs lithium salts of dipyrrins as intermediates that are then treated with only one equivalent of boron ...
  • Celebrating the 200th anniversary of Dalhousie University in Halifax, Nova Scotia, Canada. 

    Thompson, A. (2018). Celebrating the 200th anniversary of Dalhousie University. Canadian Journal of Chemistry, 2018, 96(7): iii,
  • Implications of measurement error structure on the visualization of multivariate chemical data: hazards and alternatives 

    Canadian Journal of Chemistry, 2018, 96(7): 738-748,
  • Robust Synthesis of F-BODIPYs 

    Publisher's version: Beh, Michael; Douglas, Katherine; House, Kelsey; Murphy, Alexandra; Sinclair, Jackson; and Thompson, Alison. Robust Synthesis of F-BODIPYs. Org. Biomol. Chem. 2016, 14, 11473-11479. DOI: 10.1039/c6ob02238c
    F-BODIPYs are widely used in applications that rely upon their highly tunable optical properties. A protocol is established for the high-yielding synthesis of F-BODIPYs involving non-anhydrous reagents and not requiring ...

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