Browsing Thompson, Alison by Issue Date

Now showing items 21-40 of 57

  • 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

  • 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

  • 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 ...

  • 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 ...

  • 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

  • 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. https://doi.org/10.1139/cjc-2014-0516
    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 ...

  • 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, ...

  • 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 ...

  • 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 ...

  • 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. https://doi.org/10.1139/cjc-2014-0364
    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 ...

  • 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 ...

  • Conversion of F-BODIPYs to Cl-BODIPYs: Enhancing the Reactivity of F-BODIPYs 

    Lundrigan, Travis, and Alison Thompson. 2013. "Conversion of F-BODIPYs to Cl-BODIPYs: Enhancing the Reactivity of F-BODIPYs." Journal of Organic Chemistry 78(2): 757-761.
    A new method for the synthesis of Cl-BODIPYs from F-BODIPYs is reported, merely requiring treatment of the F-BODIPY with boron trichloride. Cl-BODIPYs are exploited as synthetic intermediates generated in situ for the ...

  • Investigations regarding the utility of prodigiosenes to treat leukemia 

    Smithen, Deborah A., A. Michael Forrester, Dale P. Corkery, Graham Dellaire, et al. 2013. "Investigations regarding the utility of prodigiosenes to treat leukemia." Organic & Biomolecular Chemistry 11(1): 62-68.
    Prodigiosenes, possessing a 4-methoxypyrrolyldipyrrin skeleton, are known for their anti-cancer activity. Structural modification of the C-ring resulted in a series of prodigiosenes that displayed promising activity against ...

  • Synthesis and characterisation of the unsubstituted dipyrrin and 4,4-dichloro-4-bora-3a,4a-diaza-s-indacene: improved synthesis and functionalisation of the simplest BODIPY framework 

    Groves, Brandon R., Sarah M. Crawford, Travis Lundrigan, Cherif F. Matta, et al. 2013. "Synthesis and characterisation of the unsubstituted dipyrrin and 4,4-dichloro-4-bora-3a,4a-diaza-s-indacene: improved synthesis and functionalisation of the simplest BODIPY framework." Chemical Communications 49(8): 816-818.
    An improved and scalable synthesis of the unsubstituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene framework facilitates access to the previously unreported parent dipyrrin HCl salt, as well as 4,4-dichloro-4-bora-3a,4a- ...

  • Synthetic prodigiosenes and the influence of C-ring substitution on DNA cleavage, transmembrane chloride transport and basicity 

    Rastogi, Soumya, Estelle Marchal, Imam Uddin, Brandon Groves, et al. 2013. "Synthetic prodigiosenes and the influence of C-ring substitution on DNA cleavage, transmembrane chloride transport and basicity." Organic & Biomolecular Chemistry 11(23): 3834-3845.
    No abstract available.

  • 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 ...

  • 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 ...

  • Synthesis of heteroleptic pyrrolide/bipyridyl complexes of ruthenium(II) 

    Lundrigan, Travis, Carla L. M. Jackson, Md Imam Uddin, Lloyd A. Tucker, et al. 2012. "Synthesis of heteroleptic pyrrolide/bipyridyl complexes of ruthenium(II)." Canadian Journal of Chemistry-Revue Canadienne De Chimie 90(8): 693-700.
    The synthesis and characterization of the first heteroleptic pyrrolide/2,2'-bipyridyl complexes of ruthenium(II) are reported. Pyrroles substituted at the 2-position with X = O functionality react with Ru(bipy)(2)Cl-2.2H(2)O ...