Browsing Thompson, Alison by Title

Now showing items 38-57 of 57

  • Step-wise synthetic approach is necessary to access g-conjugates of folate: folate-conjugated prodigiosenes 

    Despite the vast literature that describes reacting folic acid with a pharmacophore, this route is ineffective in providing the correct regioisomer of the resulting conjugate. We herein present a step-wise route to the ...

  • 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 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 ...

  • 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 ...

  • 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- ...

  • 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 ...

  • 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

  • Synthesis and reactivity of 2-thionoester pyrroles: a route to 2-formyl pyrroles 

    Kim, Min Joon; Gaube, Sophie M.; Beh, Michael H. R.; Smith, Craig D.; Thompson, Alison. (2019). RSC Advances.
    2-Functionalised pyrroles exhibit considerable synthetic utility. Herein, the synthesis and reactivity of 2-thionoester (-C(S)OR) pyrroles is reported. 2-Thionoester pyrroles were synthesized using a Knorr-type approach ...

  • 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 ...

  • Synthesis of dipyrrins bearing chirality adjacent to the conjugated skeleton - Electron-poor pyrroles exhibit dramatically reduced nucleophilicity 

    Beshara, Cory S., Beth M. Pearce, and Alison Thompson. 2008. "Synthesis of dipyrrins bearing chirality adjacent to the conjugated skeleton - Electron-poor pyrroles exhibit dramatically reduced nucleophilicity." Canadian Journal of Chemistry-Revue Canadienne De Chimie 86(10): 951-957.
    With the aim of furthering our investigations into the asymmetric complexation of dipyrrinato ligands, a dipyrrin bearing a stereogenic centre directly adjacent to the conjugated skeleton was synthesized. The electron- ...

  • 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 ...

  • Synthesis of natural products containing the pyrrolic ring 

    Young, Ian S., Paul D. Thornton, and Alison Thompson. 2010. "Synthesis of natural products containing the pyrrolic ring." Natural Product Reports 27(12): 1801-1839.
    This review provides an overview of the synthetic chemistry that has been utilised to prepare natural products containing a pyrrolic ring.

  • 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 ...

  • Synthesis of sulfenyl dipyrroles via reaction of a-free pyrroles with thionyl chloride 

    Beh, Michael H. R.; Smith, Craig D.; Robertson, Katherine N.; and Thompson, Alison. (2020). Synthesis of sulfenyl dipyrroles via reaction of a-free pyrroles with thionyl chloride. Canadian Journal of Chemistry,

  • 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 ...

  • Synthesis, properties and reactivity of BCl2 aza-BODIPY complexes and salts of the aza-dipyrrinato scaffold 

    Diaz-Rodriguez, R. M., Burke, L., Robertson, K. N., & Thompson, A. (2020). Synthesis, properties and reactivity of BCl 2 aza-BODIPY complexes and salts of the aza-dipyrrinato scaffold. Organic & Biomolecular Chemistry, 18(11), 2139-2147.
    The synthesis and characterisation of the BCl2-chelated complexes of both archetypal aza-dipyrrin sub- types are presented. A stepwise halogen exchange, leading to a mixed-halide Cl–B–F intermediate, is implicated in the ...

  • 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.

  • 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

  • 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 ...

  • 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 ...