Brassinosteroids: synthesis and activity of some fluoro analogues.
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.
Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Fleming Square 2, 166 10 Prague 6, Czech Republic.
Barbora
B
Slavikova
Ladislav
L
Kohout
Milos
M
Budesinsky
Jana
J
Swaczynova
Alexander
A
Kasal
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D060406:Brassinosteroids; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D002777:Cholestanols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017611:Fluorine Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D013260:Steroids, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D060406:Brassinosteroids; D002777:Cholestanols; D017611:Fluorine Compounds; D013260:Steroids, Heterocyclic; C023623:brassinolide