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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 ...
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, ...
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 ...
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). ...
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 ...
Synthesis of Prodigiosene-Estrogen Conjugates: optimization of protecting group strategies and anticancer properties
(Canadian Journal of Chemistry, 2015)
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 ...
Step-wise synthetic approach is necessary to access g-conjugates of folate: folate-conjugated prodigiosenes
(2019)
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 ...