1039731-32-2Relevant academic research and scientific papers
Brassinosteroids: Synthesis and activity of some fluoro analogues
Slavikova, Barbora,Kohout, Ladislav,Budesinsky, Milos,Swaczynova, Jana,Kasal, Alexander
, p. 3979 - 3984 (2008)
Three types of 5α-androstane and ergostane analogues of brassinolide, containing a fluorine atom in either the 3α or the 5α positions or in 3α and 5α positions, were prepared using standard operations (reaction of 3β-alcohols with (diethylamino)sulfur trifluoride, cleavage of epoxide with HF in py or BF3·Et2O). The 5α-fluorine was found to affect chemical reactivity (e.g., electrophilic addition to the Δ2-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.
