6468-55-9Relevant articles and documents
Total synthesis of demethylwedelolactone and wedelolactone by Cu-mediated/Pd(0)-catalysis and oxidative-cyclization
Chang, Chia-Fu,Yang, Ling-Yi,Chang, Shiao-Wei,Fang, Yu-Ting,Lee, Yean-Jang
, p. 3661 - 3666 (2008/09/20)
Hedysarimcoumestan B, which can be isolated from Chinese herbal medicine, is achieved, in which the longest linear sequence is only eight steps, in 50% overall yield from commercially available phloroglucinol. The key transformations in the synthesis are Cu-mediated/Pd(0)-catalysis and I2/pyridine oxidative-cyclization reactions. This synthetic strategy can be applied to give access to the demethylwedelolactone (4) and wedelolactone (5), which were afforded from commercially available phloroglucinol in high 38 and 33% yields, respectively.
Wedelolactone and coumestan derivatives as new antihepatotoxic and antiphlogistic principles
Wong,Antus,Gottsegen,Fessler,Rao,Sonnenbichler,Wagner
, p. 661 - 665 (2007/10/02)
For the study of structure-activity relationships, the antihepatotoxic wedelolactone (7-methoxy-5,11,12-trihydroxy-coumestan) and 6 coumestan derivatives were synthesized by the application of a modified method of Wanzlich. An evaluation of the biological characteristics of the synthetic compounds and acuminatin from Musa acuminata showed that most of the wedelolactone derivatives significantly protected primary cultured liver cells from the toxicity of CCl4, galactosamine (Galc), and phalloidin, and strongly inhibited the activity of 5-lipoxygenase in porcine leukocytes. The hepatocyte protective activity was dependent on the C-7 substitution with pharmacological efficacy decreasing in the following order: EtO > MeO > OH > CH3(CH2)9. In addition, a free OH at C-5 of the wedelolactone molecule was shown to be important in protecting hepatocytes from CCl4 and Galc damage. Similar observation regarding the effect of C-7 substitution in wedelolactone was obtained in the 5-lipoxygenase test. In general, an increase in the lipophilicity in ring A increased the inhibition of 5-lipoxygenase activity. The synthetic wedelolactone was also found to have stimulatory effect on the RNA synthesis in isolated nuclei from hepatocytes.
Electrochemical Synthesis of Heterocyclic Compounds. XII. Anodic Oxidation of Catechol in the Presence of Nucleophiles
Tabakovic, Ibro,Grujic, Zdravko,Bejtovic, Zlatko
, p. 635 - 638 (2007/10/02)
The electrochemical synthesis of coumestan derivatives and some related heterocyclic system (2a-11a) by anodic oxidation of catechol (1) in the presence of various nucleophiles 2-11 is described.Products were obtained in good yields and purity.The mechanism of oxidation was deduced from voltammetric data and by coulometry at controlled potential.