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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, ...
Robust Synthesis of F-BODIPYs
(Royal Society of Chemistry, 2016)
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 ...
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 ...
The Use of Tin (IV) Chloride to Selectively Cleave Benzyl Esters over Benzyl Ethers and Benzyl Amines
(Canadian Journal of Chemistry, 2014)
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 ...
Regioselective Substituent Effects upon the Synthesis of Dipyrrins from 2-Formyl Pyrroles
(Canadian Journal of Chemistry, 2018)
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 ...