Evanno L. auteur aut IRD Lachkar D. auteur aut IRD Lamali A. auteur aut IRD Boufridi A. auteur aut IRD Seon-Meniel B. auteur aut IRD Tintillier F. auteur aut IRD Saulnier D. auteur aut IRD Denis S. auteur aut IRD Genta-Jouve G. auteur aut IRD Jullian J. C. auteur aut IRD Leblanc K. auteur aut IRD Beniddir M. A. auteur aut IRD Petek Sylvain auteur aut IRD Debitus Cécile auteur aut IRD Poupon E. auteur aut IRD text journalArticle eng text/pdf born digital access We report herein a ring-distortion strategy applied to marine natural substances ilimaquinone and 5-epi-ilimaquinone. A chemically diverse library of molecules was synthesised that included rearrangements of the sesquiterpene moiety and original reorganisations of the quinone ring. Chemoinformatic analyses evaluated the rise of structural diversity and the exploration of chemical space. Some focussed biological activities of this library were also investigated; quorum sensing activity of Vibrio harveyi was envisaged and some of the new compounds were shown to be good quorum sensing inhibitor candidates, whereas others were activators. Toxicities were also evaluated and some products showed micromolar activities against human umbilical vein endothelium, human hepatocellular carcinoma and human lung carcinoma (A549) cells. specialized Synthetic methods Ilimaquinone Ring-distortion Quinones Molecular diversity Quorum sensing 035 020 20-21 2486-2497 2018 1434-193X https://www.documentation.ird.fr/hor/fdi:010073101 10.1002/ejoc.201800047 1434-193X [F B010073101] https://www.documentation.ird.fr/hor/fdi:010073101 https://www.documentation.ird.fr/intranet/publi/2018/06/010073101.pdf Accès réservé (Intranet de l'IRD) IRD - Base Horizon / Pleins textes 2018-07-03 2023-07-11 fdi:010073101 fre