388566-83-4Relevant academic research and scientific papers
Conjugation of Hydroxytyrosol with Other Natural Phenolic Fragments: From Waste to Antioxidants and Antitumour Compounds
Tassano, Erika,Alama, Angela,Basso, Andrea,Dondo, Giancarlo,Galatini, Andrea,Riva, Renata,Banfi, Luca
, p. 6710 - 6726 (2015/10/29)
Hydroxytyrosol, a natural polyphenol that can be extracted from olive mill waste waters, was converted into a series of more complex and lipophilic analogues by conjugation with other naturally derived (poly)phenolic fragments. Ether and triazole linkers were employed. A small library of compounds was prepared, stressing step economy and operational simplicity. Some of these substances were proven to have activity equal or superior to that of the parent hydroxytyrosol in radical scavenging assays as well as in cytotoxicity tests against tumour cells.
Novel syntheses of cis and trans isomers of combretastatin A-4
Gaukroger, Keira,Hadfield, John A.,Hepworth, Lucy A.,Lawrence, Nicholas J.,McGown, Alan T.
, p. 8135 - 8138 (2007/10/03)
A high-yielding, two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 (1) has been devised. The method uses the Perkin condensation of 3,4,5-trimethoxyphenylacetic acid and 3-hydroxy-4-methoxybenzaldehyde followed by decarboxylation of the cinnamic acid intermediate using copper and quinoline. The iodine-catalyzed isomerization of the Z isomer 1 results in complete conversion to the E isomer. The Suzuki cross-coupling of an aryl boronic acid and vinyl bromide has also been successfully employed to produce both Z and E isomers of combretastatin A-4 stereoselectively. Both methods are far superior to the current five-step Wittig synthesis in which both isomers are produced nonstereoselectively.
