Q56973513
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To identify novel estrogen receptor ligands a series of substituted 17alpha-arylestradiols were synthesized using the catalytic [2 + 2 + 2]cyclotrimerization of 17alpha-ethynylestradiol with various 1,7-diynes in the presence of Wilkinson's catalysts [Rh(PPh(3))(3)Cl]. The compounds were subjected to competitive binding assays, cell-based luciferase reporter assays, and proliferation assays. These experiments confirmed their estrogenic character and revealed some interesting properties like mixed partial/full agonism for ERalpha/ERbeta and different selectivity as a result of differing potencies for either ER.
- MeSH
- aktivace transkripce MeSH
- alfa receptor estrogenů agonisté genetika MeSH
- alkyny chemie MeSH
- beta receptor estrogenů agonisté genetika MeSH
- buněčné linie MeSH
- cyklizace MeSH
- estradiol analogy a deriváty chemická syntéza farmakologie MeSH
- fluorescenční polarizace MeSH
- kompetitivní vazba MeSH
- lidé MeSH
- ligandy MeSH
- luciferasy genetika MeSH
- nádorové buněčné linie MeSH
- parciální agonismus léků MeSH
- proliferace buněk účinky léků MeSH
- reportérové geny MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
Three types of brassinosteroid analogues with perfluoroalkylated side chains were synthesized by using alkene cross-metathesis of a brassinosteroid derivative bearing a terminal alkene moiety with different (perfluoroalkyl)propenes. The presence of the double bonds in the cross-metathesis products allowed a facile one-step double dihydroxylation to provide intermediates that after Baeyer-Villiger oxidation afforded the target compounds. Biological activity of the prepared analogues was tested in GABA(A) receptor, cytotoxic, and brassinolide activity, which reached in some cases the same range as their nonfluorinated analogues.
- MeSH
- alkeny chemie MeSH
- biotest MeSH
- cholestanoly farmakologie MeSH
- krysa rodu rattus MeSH
- lidé MeSH
- nádorové buněčné linie MeSH
- objevování léků MeSH
- potkani Wistar MeSH
- protinádorové látky farmakologie chemická syntéza chemie metabolismus MeSH
- receptory GABA-A metabolismus MeSH
- steroidy heterocyklické farmakologie MeSH
- steroidy chemická syntéza chemie metabolismus farmakologie MeSH
- zvířata MeSH
- Check Tag
- krysa rodu rattus MeSH
- lidé MeSH
- mužské pohlaví MeSH
- zvířata MeSH
- Publikační typ
- práce podpořená grantem MeSH
