Synthesis of novel aryl brassinosteroids through alkene cross-metathesis and preliminary biological study

0481221 - ÚEB 2018 RIV US eng J - Journal Article
Kořínková, Petra - Bazgier, V. - Oklešťková, Jana - Rárová, L. - Strnad, Miroslav - Kvasnica, Miroslav
Synthesis of novel aryl brassinosteroids through alkene cross-metathesis and preliminary biological study.
Steroids. Roč. 127, NOV (2017), s. 46-55. ISSN 0039-128X. E-ISSN 1878-5867
R&D Projects: GA ČR GJ15-08202Y; GA MŠMT(CZ) LO1204
Institutional support: RVO:61389030
Keywords : Brassinosteroids * BRI1 receptor kinase * Cross-metathesis * Molecular docking * Organic synthesis * Plant bioassays
OECD category: Organic chemistry
Impact factor: 2.523, year: 2017

A series of phenyl analogues of brassinosteroids was prepared via alkene cross-metathesis using commercially available styrenes and 24-nor-5α-chola-2,22-dien-6-one. All derivatives were successfully docked into the active site of BRI1 using AutoDock Vina. Plant growth promoting activity was measured using the pea inhibition biotest and Arabidopsis root sensitivity assay and then was compared with naturally occuring brassinosteroids. Differences in the production of plant hormone ethylene were also observed in etiolated pea seedlings after treatment with the new and also five known brassinosteroid phenyl analogues. Antiproliferative activity was also studied using normal human fibroblast and human cancer cell lines.
Permanent Link: http://hdl.handle.net/11104/0276819