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Decarboxylative Arylation of Substituted Pyrroles N-protected with 2-(Trimethylsilyl) ethoxymethyl (SEM)
(Canadian Journal of Chemistry, 2018)
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 ...
Synthesis and biological evaluation of prodigiosene conjugates of porphyrin, estrone and 4-hydroxytamoxifen
(Bioorganic & Medicinal Chemistry, 2013)
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
(Organic Letters, 2012)
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.
(Canadian Journal of Chemistry, 2018)
Influence of B-Ring Modifications on Proton Affinity, Transmembrane Anion Transport and Anti-Cancer Properties of Synthetic Prodigiosenes
(Organic and Biomolecular Chemistry, 2014)
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, ...
Use of F-BODIPYs as a protection strategy for dipyrrins: optimization of BF2 removal.
(Journal of Organic Chemistry, 2012)
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
(Organic and Biomolecular Chemistry, 2014)
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 Characterization of Pyrrolyldipyrrin F-BODIPYs
(Photochemical and Photobiological Sciences, 2018)
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
(2018)
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). ...
Activation and Deprotection of F-BODIPYs using Boron Trihalides
(2014)
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 ...