Browsing Thompson, Alison by Author "26380f56-a3d0-4bc3-802d-6cd93ead0448"
Now showing items 1-20 of 25
-
Activation and Deprotection of F-BODIPYs using Boron Trihalides
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 ... -
Bis[Pyrrolyl Ru(II)] Triads: a New Class of Photosensitizers for Metal-Organic Photodynamic Therapy
A new family of ten dinuclear Ru(II) complexes based on the bis[pyrrolyl Ru(II)] triad scaffold, where two Ru(bpy)2 centers are separated by a variety of organic linkers, was prepared to evaluate the influence of the ... -
Bridging and Conformational Control of Porphyrin Units through Non-Traditional Rigid Scaffolds
Connecting two porphyrin units in a rigid linear fashion, without any undesired electron delocalization or communication between the chromophores, remains a synthetic challenge. Herein, a broad library of functionally ... -
Bridging and Conformational Control of Porphyrin Units through Non-Traditional Rigid Scaffolds
Connecting two porphyrin units in a rigid linear fashion, without any undesired electron delocalization or communication between the chromophores, remains a synthetic challenge. Herein, a broad library of functionally ... -
Classifying donor strengths of dipyrrinato/aza-dipyrrinato ligands
A parameter is reported by which to use 13C NMR chemical shifts to measure and predict the donor capabilities of N^N dipyrrinato and aza-dipyrrinato ligands chelating in L^X fashion. The results enable the rationalisation ... -
Decarboxylative Arylation of Substituted Pyrroles N-protected with 2-(Trimethylsilyl) ethoxymethyl (SEM)
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 ... -
Facile Deprotection of F-BODIPYs using Methylboronic Acid
4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) are deprotected through removal of the –BF2 moiety upon treatment with methylboronic acid. The tolerance of various substitution patterns about the dipyrrinato core ... -
An Improved Method for the Synthesis of F-BODIPYs from Dipyrrins and Bis(dipyrrin)s
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 ... -
Influence of B-Ring Modifications on Proton Affinity, Transmembrane Anion Transport and Anti-Cancer Properties of Synthetic Prodigiosenes
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, ... -
Photo-induced Anticancer Activity and Singlet Oxygen Production of Prodigiosenes
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). ... -
The Photodecarboxylation of Substituted Naphthylmethyl Arylacetate Esters: Synthesis of Naphthylarylethanes
The synthesis of naphthylarylethanes via the photodecarboxylation of naphthylmethyl arylacetate esters is reported where the aryl group is able to stabilize a charge transfer reaction. The reaction proceeds via intramolecular ... -
Regioselective Substituent Effects upon the Synthesis of Dipyrrins from 2-Formyl Pyrroles
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 ... -
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 Antimalarial Activity of Prodigiosenes
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
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 Characterization of Pyrrolyldipyrrin F-BODIPYs
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 reactivity of 2-thionoester pyrroles: a route to 2-formyl pyrroles
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
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 Prodigiosene-Estrogen Conjugates: optimization of protecting group strategies and anticancer properties
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 ...
