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Eaton’s Reagent-Mediated Domino π-Cationic Arylations of Aromatic Carboxylic Acids to Iasi-Red Polymethoxylated Polycyclic Aromatic Hydrocarbons: Products with Unprecedented Biological Activities as Tubulin Polymerization Inhibitors

Abstract : A rapid domino π-cationic arylation of aromatic carboxylic acids, mediated by Eaton's reagent, has been developed for the synthesis of Iasi-red polymethoxylated polycyclic aromatic hydrocarbons (PAHs). This route is currently the easiest method to obtain such popular PAH compounds, which bear in addition numerous methoxy groups. The domino process was generalized, the structure of the obtained red products and the mechanism of their formations were elucidated, and some of their photophysical properties were determined. Newly synthesized polymethoxylated-PAHs were tested for their interaction with tubulin polymerization as well as for their cytotoxicity on a panel of NCI-60 human cancer cell lines. Interestingly, one of these rubicene derivatives exhibited remarkable cytotoxicity in vitro, including inhibition of leukemia, colon, melanoma, CNS, and ovarian cancer cell lines with GI50 values in the low nanomolar range (GI50 < 10 nM).
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02564865
Contributor : Adam Daich <>
Submitted on : Wednesday, May 6, 2020 - 9:01:35 AM
Last modification on : Wednesday, July 8, 2020 - 12:42:25 PM

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Alina Ghinet, Philippe Gautret, Nathalie Van Hijfte, Bertrand Ledé, Jean-Pierre Hénichart, et al.. Eaton’s Reagent-Mediated Domino π-Cationic Arylations of Aromatic Carboxylic Acids to Iasi-Red Polymethoxylated Polycyclic Aromatic Hydrocarbons: Products with Unprecedented Biological Activities as Tubulin Polymerization Inhibitors. Chemistry - A European Journal, Wiley-VCH Verlag, 2014, 20 (32), pp.10117-10130. ⟨10.1002/chem.201402377⟩. ⟨hal-02564865⟩

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