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A Ring‐Distortion Strategy from Marine Natural Product Ilimaquinone Leads to Quorum Sensing Modulators
Author(s) -
Evanno Laurent,
Lachkar David,
Lamali Assia,
Boufridi Asmaa,
SéonMéniel Blandine,
Tintillier Florent,
Saulnier Denis,
Denis Stéphanie,
GentaJouve Grégory,
Jullian JeanChristophe,
Leblanc Karine,
Beniddir Mehdi A.,
Petek Sylvain,
Debitus Cécile,
Poupon Erwan
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800047
Subject(s) - chemistry , quorum sensing , vibrio harveyi , chemical space , natural product , moiety , biochemistry , stereochemistry , small molecule , ring (chemistry) , combinatorial chemistry , computational biology , bacteria , drug discovery , organic chemistry , gene , vibrio , biology , genetics , virulence
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.