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Multifaceted Study on a Cytochalasin Scaffold: Lessons on Reactivity, Multidentate Catalysis, and Anticancer Properties
Author(s) -
Zaghouani Mehdi,
Gayraud Oscar,
Jactel Vincent,
Prévost Sébastien,
Dezaire Ambre,
Sabbah Michèle,
Escargueil Alexandre,
Lai ThanhLan,
Le Clainche Christophe,
Rocques Nathalie,
Romero Stéphane,
Gautreau Alexis,
Blanchard Florent,
Frison Gilles,
Nay Bastien
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804023
Subject(s) - thiourea , reactivity (psychology) , denticity , chemistry , intramolecular force , cytochalasin , cytochalasin d , scaffold , cytotoxicity , combinatorial chemistry , catalysis , stereochemistry , organic chemistry , biochemistry , cytoskeleton , cell , in vitro , computer science , medicine , alternative medicine , pathology , database , crystal structure
An intramolecular Diels–Alder (IMDA) reaction efficiently accelerated by Schreiner's thiourea is reported, to build a functionalized cytochalasin scaffold (periconiasin series) for biological purposes. 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 actin polymerization is preserved.