Now showing items 21-40 of 48

  • Asymmetric Dipyrrin and F-BODIPYs Conjugated to Terminal Alkynes and Alkenes 

    Published version: Figliola, C., Robertson, K., Greening, S., & Thompson, A. (2017). Asymmetric Dipyrrin and F-BODIPYs Conjugated to Terminal Alkynes and Alkenes. Journal of Organic Chemistry (June 24, 2017)
  • Prodigiosenes Conjugated to Tamoxifen and Estradiol 

    Published version: Marchal E1, Figliola C, Thompson A. (2017) Prodigiosenes Conjugated to Tamoxifen and Estradiol. Organic and Biomolecular Chemistry, 15(25):5410-5427. doi: 10.1039/c7ob00943g
  • Synthesis and Anticancer Activity of Prodigiosenes bearing C-Ring Esters and Amides 

    Published version: Lund, K., Figliola, C., Kajetanowicz, A. & Thompson, A. (2017) Synthesis and Anticancer Activity of Prodigiosenes bearing C-Ring Esters and Amides, RSC Advances, 50 (7), 18617. doi: 10.1039/c7ra01628j
  • Synthesis and Photobiological Activity of Ru(II) Dyads Derived from Pyrrole-2-Carboxylate Thionoesters 

    Deborah A. Smithen, Huimin Yin, Michael H. R. Beh, Marc Hetu, T. Stanley Cameron, Sherri A. McFarland,*and Alison Thompson. (2017). Inorganic Chemistry, 56, 4121-4132. DOI: 10.1021/acs.inorgchem.7b00072
  • Probing the Hydrolytic Reactivity of 2-Difluoromethyl Pyrroles 

    Published version: Melanson JA, Figliola C, Smithen DA, Kajetanowicz AK, Thompson A. (2017). Probing the Hydrolytic Reactivity of 2-Difluoromethyl Pyrroles. Organic and Biomolecular Chemistry. 15, 144-152. doi:10.1039/c6ob01441k
  • Eight-Membered Ring-Containing Jadomycins: Implications for Non-enzymatic Natural Products Biosynthesis 

    Published version: Robertson AW, Martinez-Farina CF, Smithen DA, Yin H, Monro S, Thompson A, McFarland SA, Syvitski RT, Jakeman DJ. (2015). Eight-Membered Ring-Containing Jadomycins: Implications for Non-enzymatic Natural Products Biosynthesis. Journal of the American Chemical Society, 137, 3271-3275. doi: 10.1021/ja5114672
  • Thionation Reactions of 2-Pyrrole Carboxylates 

    Brandon R. Groves, Deborah A. Smithen, T. Stanley Cameron and Alison Thompson. (2016). Thionation Reactions of 2-Pyrrole Carboxylates. RSC Advances, 6, 69691-69697. DOI: 10.1039/c6ra14809c
  • 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 ...
  • 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, https://doi.org/10.1139/cjc-2018-0190
  • 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 ...
  • 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 ...
  • 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: https://doi.org/10.1139/cjc-2013-0341
    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 ...
  • 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: https://doi.org/10.1139/cjc-2017-0402
    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 ...
  • 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, ...
  • 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 ...
  • 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 ...
  • 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 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 ...
  • 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 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 ...