114211-87-9Relevant academic research and scientific papers
Brassinosteroids: Synthesis and activity of some fluoro analogues
Slavikova, Barbora,Kohout, Ladislav,Budesinsky, Milos,Swaczynova, Jana,Kasal, Alexander
supporting information; experimental part, p. 3979 - 3984 (2009/04/07)
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.
ALTERNATIVE SYNTHESES OF 2α,3α,17β-TRIHYDROXY-7-OXA-B-HOMO-5α-ANDROSTAN-6-ONE AND SOME ANDROSTANE BRASSINOLIDE ANALOGS
Kohout, Ladislav,Cerny, Vaclav,Strnad, Miroslav
, p. 1026 - 1042 (2007/10/02)
The title compound XVI was synthesized from III, IV or V.Related compounds X, XIII, XVI, XVIII, XXIII, XXIV, XXVII, XXVIII, XXXV, XXXVI, XLI, and XLIII were also prepared and tested by bean second internode bioassay.They showed only low activity (by about
