35675-93-5Relevant academic research and scientific papers
Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues
Ding, De-Jun,Cao, Xiao-Yan,Dai, Fang,Li, Xiu-Zhuang,Liu, Guo-Yun,Lin, Dong,Fu, Xing,Jin, Xiao-Ling,Zhou, Bo
, p. 1011 - 1019 (2012/11/07)
Five hydroxylated phenanthrenes as "cis-configuration-fixed" resveratrol analogues differing in the number and position of the hydroxyl groups were designed and synthesized. Their antioxidant activity was studied by ferric reducing antioxidant power, 2,2-diphenyl-1-picrylhydrazyl free radical-scavenging, and DNA strand breakage-inhibiting assays, corresponding to their electron-donating, hydrogen-transfer and DNA-protecting abilities, respectively. In the above assays, their activity depends significantly on the number and position of the hydroxyl groups, and most of them are more effective than resveratrol. Noticeably, compound 9b (2,4,6-trihydroxyl phenanthrene) with the same hydroxyl group substitutions as resveratrol, is superior to the reference compound, highlighting the importance of extension of the conjugation over multiple aromatic-rings. Similar activity sequences were obtained in different experimental models, but the appreciable differences could contribute detailed insights into antioxidant mechanisms. Based on these results, the hydroxylated phenanthrenes may be considered as a novel type of resveratrol-directed antioxidants.
Intramolecular Biaryl Oxidative Coupling of Stilbenes by Vanadium Oxytrichloride (VOCl3): Facile Synthesis of Substituted Phenanthrene Derivatives
Jin, Zhong,Wang, Qingmin,Huang, Runqiu
, p. 119 - 128 (2007/10/03)
Vanadium oxytrichloride (VOCl3) has proven to be a highly efficient reagent for intramolecular biaryl oxidative coupling reaction of electron-rich stilbenes. Accordingly, a mild and efficient route to phenanthrene derivatives from stilbenes oxy
The Oxidative Conversion of (E)-α-(Arylmethylene)-benzeneacetates into Substituted Phenanthrenes: The Propitious Use of Boron Trifluoride with Vanadium trifluoride Oxide
Halton, Brian,Maidment, Andrew I.,Officer, David L.,Warnes, Jeremy M.
, p. 2119 - 2128 (2007/10/02)
Vanadium trifluoride oxide (VOF3)/boron trifluoride diethyl etherate is especially useful for effecting the cyclization of the (E)-α-(arylmethylene)benzeneacetates (4a,b,d) to the substituted phenanthrenes (5a,b,d).The products are obtained in 20 percent higher yield and under milder conditions than by employing the vanadium reagent with trifluoroacetic acid.A survey of the derivatives (4a-n) has shown that oxygen functionality is necessary at the 3- and 4- and/or the 3'- and 4'-positions of (4) for cyclization to occur.
