21390-25-0Relevant academic research and scientific papers
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.
, 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.
Homo- and hetero-oxidative coupling of benzyl anions
Blangetti, Marco,Fleming, Patricia,O'Shea, Donal F.
experimental part, p. 2870 - 2877 (2012/04/23)
The regioselective benzylic metalation of substituted toluenes using BuLi/KO-t-Bu/TMP(H) (LiNK metalation conditions) with subsequent in situ oxidative C-C coupling has been developed for the facile generation of 1,2-diarylethanes. A range of oxidants can be used for the oxidative coupling step, with 1,2-dibromoethane proving optimal. Heterocouplings can be achieved starting from a mixture of two different toluenes with a bias toward cross coupling achievable by using a 2-fold excess of one toluene starting material. The utility of this approach is illustrated by the synthesis of several biologically active natural products. A distinct advantage is that the synthetic steps typically required to preactivate the coupling substrates are eliminated and no transition metal is required to facilitate the C-C bond formation.
New Drug Delivery System for Crossing the Blood Brain Barrier
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Page/Page column 30, (2008/06/13)
New ubiquinol analogs are disclosed, as well as methods of using these compounds to deliver drug moieties to the body.
REGIOSELECTIVE REDUCTIVE ALKYLATION OF 1,2,3-TRIMETHOXYBENZENE
Azzena, Ugo,Cossu, Sergio,Denurra, Teresa,Melloni, Giovanni,Piroddi, Anna Maria
, p. 1689 - 1690 (2007/10/02)
The 2-methoxyl group of 1,2,3-trimethoxybenzene and its 5-methyl-substituted homologue is removed under electron transfer conditions and replaced with an alkyl group in a one-pot procedure.
