249504-85-6Relevant articles and documents
Nickel-catalyzed carboannulation reaction of o-bromobenzyl zinc bromide with unsaturated compounds
Deng, Ruixue,Sun, Liangdong,Li, Zhi
, p. 5207 - 5210 (2007)
(Chemical Equation Presented) A number of indenes have been prepared in good yields by treating o-bromobenzyl zinc bromide 1 with various terminal and internal alkynes in the presence of a nickel catalyst. The nickel-catalyzed carboannulation reaction was successfully extended to the synthesis of indane derivatives by reaction of 1 with acrylates and styrene.
Monocyclic Quinone Structure-Activity Patterns: Synthesis of Catalytic Inhibitors of Topoisomerase II with Potent Antiproliferative Activity
Waugh, Thomas M.,Masters, John,Aliev, Abil E.,Marson, Charles M.
supporting information, p. 114 - 124 (2019/12/11)
The monocyclic 1,4-benzoquinone, HU-331, the direct oxidation product of cannabidiol, inhibits the catalytic activity of topoisomerase II but without inducing DNA strand breaks or generating free radicals, and unlike many fused-ring quinones exhibits minimal cardiotoxicity. Thus, monocyclic quinones have potential as anticancer agents, and investigation of the structural origins of their biological activity is warranted. New syntheses of cannabidiol and (±)-HU-331 are here reported. Integrated synthetic protocols afforded a wide range of polysubstituted resorcinol derivatives; many of the corresponding novel 2-hydroxy-1,4-benzoquinone derivatives are potent inhibitors of the catalytic activity of topoisomerase II, some more so than HU-331, whose monoterpene unit replaced by a 3-cycloalkyl unit conferred increased antiproliferative properties in cell lines with IC50 values extending below 1 mM, and greater stability in solution than HU-331. The principal pharmacophore of quinones related to HU-331 was identified. Selected monocyclic quinones show potential for the development of new anticancer agents.
