Domino approach to 2-aroyltrimethoxyindoles as novel heterocyclic combretastatin A4 analogues.
Two series of 2-aroyltrimethoxyindoles were designed to investigate the effects of the replacement of the trimethoxyphenyl ring of phenstatin with a trimethoxyindole moiety. These compounds were efficiently prepared through a domino palladium-catalyzed sequence from 2-gem-dibromovinylanilines substituted by three methoxy groups and arylboronic acids under carbon monoxide atmosphere. These novel heterocyclic combretastatin A4 analogues were evaluated for their cell growth inhibitory properties and their ability to inhibit the tubulin polymerization.
Institut Curie, Centre de Recherche, 26 rue d'Ulm, Paris F-75248 cedex 05, France.
Martin
M
Arthuis
Renée
R
Pontikis
Guy G
GG
Chabot
Lionel
L
Quentin
Daniel
D
Scherman
Jean-Claude
JC
Florent
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D055808:Drug Discovery / Q000379:methods*; D006571:Heterocyclic Compounds / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D007211:Indoles / Q000737:chemistry* / Q000494:pharmacology*; D051379:Mice; D055503:Protein Multimerization / Q000187:drug effects; D020836:Protein Structure, Quaternary; D013267:Stilbenes / Q000737:chemistry* / Q000494:pharmacology*; D014404:Tubulin / Q000737:chemistry
D000970:Antineoplastic Agents; D006571:Heterocyclic Compounds; D007211:Indoles; D013267:Stilbenes; D014404:Tubulin; C058728:fosbretabulin