Evanno L., Lachkar D., Lamali A., Boufridi A., Seon-Meniel B., Tintillier F., Saulnier D., Denis S., Genta-Jouve G., Jullian J. C., Leblanc K., Beniddir M. A., Petek Sylvain, Debitus Cécile, Poupon E. (2018). A ring-distortion strategy from marine natural product ilimaquinone leads to quorum sensing modulators. European Journal of Organic Chemistry, 20-21, p. 2486-2497. ISSN 1434-193X.
Titre du document
A ring-distortion strategy from marine natural product ilimaquinone leads to quorum sensing modulators
Année de publication
2018
Auteurs
Evanno L., Lachkar D., Lamali A., Boufridi A., Seon-Meniel B., Tintillier F., Saulnier D., Denis S., Genta-Jouve G., Jullian J. C., Leblanc K., Beniddir M. A., Petek Sylvain, Debitus Cécile, Poupon E.
Source
European Journal of Organic Chemistry, 2018,
20-21, p. 2486-2497 ISSN 1434-193X
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.
Plan de classement
Sciences fondamentales / Techniques d'analyse et de recherche [020]
;
Substances naturelles [035]
Localisation
Fonds IRD [F B010073101]
Identifiant IRD
fdi:010073101
