Design, synthesis and biological activities of new brassinosteroid analogues with a phenyl group in the side chain
Language English Country England, Great Britain Media print
Document type Journal Article
PubMed
27714217
DOI
10.1039/c6ob01479h
Knihovny.cz E-resources
- MeSH
- Antineoplastic Agents chemistry metabolism pharmacology MeSH
- Arabidopsis metabolism MeSH
- Brassinosteroids chemistry metabolism pharmacology MeSH
- Humans MeSH
- Cell Line, Tumor MeSH
- Neoplasms drug therapy MeSH
- Protein Kinases metabolism MeSH
- Arabidopsis Proteins metabolism MeSH
- Plant Growth Regulators metabolism MeSH
- Molecular Docking Simulation MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Antineoplastic Agents MeSH
- Brassinosteroids MeSH
- BRI1 protein, Arabidopsis MeSH Browser
- Protein Kinases MeSH
- Arabidopsis Proteins MeSH
- Plant Growth Regulators MeSH
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.
References provided by Crossref.org
Synthesis of New Brassinosteroid 24-Norcholane Type Analogs Conjugated in C-3 with Benzoate Groups
Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side Chain
