Brassinosteroids: synthesis and activity of some fluoro analogues
Jazyk angličtina Země Spojené státy americké Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
18557605
DOI
10.1021/jm800085p
Knihovny.cz E-zdroje
- MeSH
- brassinosteroidy MeSH
- buněčné linie MeSH
- cholestanoly chemická syntéza chemie farmakologie MeSH
- lidé MeSH
- molekulární struktura MeSH
- protinádorové látky chemická syntéza chemie farmakologie MeSH
- sloučeniny fluoru chemická syntéza chemie farmakologie MeSH
- steroidy heterocyklické chemická syntéza chemie farmakologie MeSH
- viabilita buněk účinky léků MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- brassinolide MeSH Prohlížeč
- brassinosteroidy MeSH
- cholestanoly MeSH
- protinádorové látky MeSH
- sloučeniny fluoru MeSH
- steroidy heterocyklické MeSH
Three types of 5alpha-androstane and ergostane analogues of brassinolide, containing a fluorine atom in either the 3alpha or the 5alpha positions or in 3alpha and 5alpha positions, were prepared using standard operations (reaction of 3beta-alcohols with (diethylamino)sulfur trifluoride, cleavage of epoxide with HF in py or BF 3.Et 2O). The 5alpha-fluorine was found to affect chemical reactivity (e.g., electrophilic addition to the Delta (2)-double bond) as well as physical properties (e.g., NMR, chromatographic behavior) of the products. Cytotoxicity of the products was studied using human normal and cancer cell lines with 28-homocastasterone as positive control and their brassinolide type activity was established using the bean second-internode test with 24-epibrassinolide as standard. The equivalence of F and OH groups was observed in some of the active compounds. The anticancer and the brassinolide-type activity do not correlate with each other: ergostane derivatives were most active in the former test while androstane derivatives were best in the latter.
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