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Author Zaghouani, Mehdi ♦ Gayraud, Oscar ♦ Jactel, Vincent ♦ Prevost, Sébastien ♦ Dezaire, Ambre ♦ Sabbah, Michèle ♦ Escargueil, Alexandre E. ♦ Lai, Thanh-Lan ♦ Le Clainche, Christophe ♦ Rocques, Nathalie ♦ Romero, Stéphane ♦ Gautreau, Alexis ♦ Blanchard, Florent ♦ Frison, Gilles ♦ Nay, Bastien
Source Hyper Articles en Ligne (HAL)
Content type Text
Publisher Wiley-VCH Verlag
File Format PDF
Language English
Subject Keyword chim ♦ Chemical Sciences ♦ Chemical Sciences/Organic chemistry
Abstract We report an intramolecular Diels-Alder reaction efficiently accelerated by Schreiner's thiourea, to build a functionalized cytochalasin scaffold (periconiasin series) amenable to biological purpose. DFT calculation highlighted a unique multidentate cooperative hydrogen bonding in this catalysis. The deprotection end-game afforded a collection of diverse structures and showed the peculiar reactivity of the Diels-Alder cycloadducts upon functionalization. Biological studies revealed strong cytotoxicity of a few compounds on breast cancer cell lines, while preserving actin polymerization.
ISSN 09476539
Educational Use Research
Learning Resource Type Article
Publisher Date 2018-11-07
e-ISSN 15213765
Journal Chemistry - A European Journal
Volume Number 24
Issue Number 62
Page Count 6
Starting Page 16686
Ending Page 16691