162547-58-2Relevant academic research and scientific papers
Synthesis of novel aryl brassinosteroids through alkene cross-metathesis and preliminary biological study
Korinkova, Petra,Bazgier, Vaclav,Oklestkova, Jana,Rarova, Lucie,Strnad, Miroslav,Kvasnica, Miroslav
, p. 46 - 55 (2017/10/06)
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.
Biological Activity of Brassinosteroids – Direct Comparison of Known and New Analogs in planta
Wendeborn, Sebastian,Lachia, Mathilde,Jung, Pierre M. J.,Leipner, J?rg,Brocklehurst, David,De Mesmaeker, Alain,Gaus, Katharina,Mondière, Régis
, (2017/02/26)
A systematic investigation of structural modifications of brassinosteroids is presented. We describe in detail their synthetic preparation, which includes significant improvements of previously reported protocols as well as access to new analogs with functional modifications of the steroid skeleton and of the C(17)-attached side chain. We report the biological potency of the prepared brassinosteroid analogs as plant hormones, which were carefully established in the French bean second internode elongation assay and discuss our observations in light of the recently reported structural data detailing the molecular interactions between brassinolide in the trimeric complex with the protein receptors kinases BRASSINOSTEROID INSENSITIVE 1 (BRI1) and SOMATIC EMBRYOGENESIS RECEPTOR KINASE 1 (SERK1). In a further part of this work we describe the preparation of H2O-soluble pro-forms of 24-epicastasterone and we discuss their physical properties, hydrolytic stabilities and biological activity.
Design, synthesis and biological activities of new brassinosteroid analogues with a phenyl group in the side chain
Kvasnica,Oklestkova,Bazgier,Rárová,Korinkova,Mikulík,Budesinsky,Béres,Berka,Lu,Russinova,Strnad
supporting information, p. 8691 - 8701 (2016/10/03)
We have prepared and studied a series of new brassinosteroid derivatives with a p-substituted phenyl group in the side chain. To obtain the best comparison between molecular docking and biological activities both types of brassinosteroids were synthesized; 6-ketones, 10 examples, and B-lactones, 8 examples. The phenyl group was introduced into the steroid skeleton by Horner-Wadsworth-Emmons. The docking studies were carried out using AutoDock Vina 1.05. Plant biological activities were established using different brassinosteroid bioassays in comparison with natural brassinosteroids. Differences in the production of the plant hormone ethylene were also observed in etiolated pea seedlings after treatment with new brassinosteroids. The most active compounds were lactone 8f and 6-oxo derivatives 8c and 9c, their biological activities were comparable or even better than naturally occurring brassinolide. Finally the cytotoxicity of the new derivatives was studied using human normal and cancer cell lines.
Studies on Steroidal Plant-growth Regulators. Part 33. Novel Method for Construction of the Side-chain of 23-Arylbrassinosteroids via Heck Arylation and Asymmetric Dihydroxylation as Key Step
Huang, Liang-Fu,Zhou, Wei-Shan
, p. 3579 - 3586 (2007/10/02)
An efficient method for construction of the 23-arylbrassinosteroidal side-chain is described via Heck coupling and asymmetric osmylation as key steps.Several new (22R,23R)-23-arylbrassinosteroids were synthesised.The overall yields of 23-phenylbrassinoste
