154013-27-1Relevant articles and documents
Total synthesis and biological evaluation of viscolin, a 1,3-diphenylpropane as a novel potent anti-inflammatory agent
Su, Chung-Ren,Shen, Yuh-Chiang,Kuo, Ping-Chung,Leu, Yann-Lii,Damu, Amooru G.,Wang, Yea-Hwey,Wu, Tian-Shung
, p. 6155 - 6160 (2006)
Total synthesis of viscolin, an anti-inflammatory 1,3-diphenylpropane isolated from Viscum coloratum, employing the Wittig reaction is reported. Key steps in the synthesis of viscolin depend on the selection of protecting groups to maintain the para hydroxyl group that is the most critical chemical structure influencing the biological activity of viscolin and the utilization of microwave-assisted Wittig olefination reaction. Anti-inflammatory potency of the synthetic viscolin, its precursor product 16, and its analogue 17, through their effects on reactive oxygen species (ROS), nitric oxide (NO), and pro-inflammatory cytokine production in leukocytes and microglial cells were evaluated. Excellent inhibition of ROS and NO production in inflammatory cells could confer the synthetic viscolin to be a potent anti-inflammatory agent for the treatment of oxidative stress-induced diseases.
Mechanistic Studies of Selective Catechol Formation from o-Methoxyphenols using a Copper(II)-Ascorbic Acid-Dioxygen System
Aihara, Kazuhiro,Urano, Yasuteru,Higuchi, Tsunehiko,Hirobe, Masaaki
, p. 2165 - 2170 (2007/10/02)
Mechanistic details of selective conversion of o-methoxyphenols to the corresponding catechols using a Cu2+-ascorbic acid-O2 system, were studied. 2,5-Dimethoxyphenol was converted predominantly to the o-demethylated compound and partially to the m-demethylated one.Anisole with no phenolic hydroxy group was much less reactive.When guaiacol (1). guaiacol and 2-methoxy-6-methoxyphenol was used as substrates, moderate intermolecular and intramolecular kinetic isotope effects were observed (1.4-1.9). Catechol was derived from 1 in nine-fold excess over catechol when the reaction was run in an 18O2 atmosphere with natural water as a solvent, though no catechol was formed when using natural O2 and H218O.It was determined that the Cu2+-ascorbic acid-O2 system operates in a monooxygenase mode because the oxygen atom of dioxygen (not water) was incorporated into the products, and this oxidative conversion proceeded mainly via ipso-substitution at the methoxy position, probably with hydroxyl radical coordinated to the cupric ion as the active oxygen species.
