Multifaceted Study on a Cytochalasin Scaffold: Lessons on Reactivity, Multidentate Catalysis, and Anticancer Properties.

Authors :: Zaghouani M
Gayraud O
Jactel V
Prévost S
Dezaire A
Sabbah M
Escargueil A
Lai TL
Le Clainche C
Rocques N
Romero S
Gautreau A
Blanchard F
Frison G
Nay B
Source :: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2018 Nov 07; Vol. 24 (62), pp. 16686-16691. Date of Electronic Publication: 2018 Oct 21.
Publication Year :: 2018
Abstract: 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.<br /> (© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

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