17241-59-7Relevant articles and documents
The Influence of Ion Pairing on the Electroreductive Cleavage of Substituted 9,10-Antraquinones in DMF Solution
Blankespoor, Ronald L.,Schutt, David L.,Tubergen, Melinda B.,De Jong, Randy L.
, p. 2059 - 2064 (1987)
A variety of substituted 9,10-antraquinones with acetates and trifluoroacetates leaving groups at the 2-methyl position were synthesized from 2-methyl-9,10-antraquinones containing 0-2 methoxy substituents.Cyclic voltammograms of the acetates in DMF containing LiClO4 as supporting electrolyte exhibited two reduction waves, the first resulting from the formation of Li(1+) ion pairs of their radical anions and the second from Li(1+) ion pairs of their dianions.Constant potential reduction of the acetates to their dianions followed by air oxidation gave high yields (78-88percent) of their reductive cleavage products, the 2-methyl-9,10-anthraquinones.In contrast, reduction of the acetates to their radical anions led to high yields of their alcohols (the 2-(hydroxymethyl)-9,10-anthraquinones) as a result of saponification.Reduction of the trifluoroacetates in DMF/LiClO4 produced comparable yields of their corresponding reductive cleavage products and alcohols via ion pairs of their radical anions or dianions.
Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues
Akhtar, Muhammad Nadeem,Zareen, Seema,Yeap, Swee Keong,Ho, Wan Yong,Lo, Kong Mun,Hasan, Aurangzeb,Alitheen, Noorjahan Banu
, p. 10042 - 10055 (2013/09/23)
Naturally occurring anthraquinones, damnacanthal (1) and nordamnacanthal (2) were synthesized with modified reaction steps and investigated for their cytotoxicity against the MCF-7 and K-562 cancer cell lines, respectively. Intermediate analogues 2-bromomethyl-1,3-dimethoxyanthraquinone (5, IC 50 = 5.70 ± 0.21 and 8.50 ± 1.18 μg/mL), 2-hydroxymethyl-1,3-dimethoxyanthraquinone (6, IC50 = 12.10 ± 0.14 and 14.00 ± 2.13), 2-formyl-1,3-dimethoxyantharquinone (7, IC 50 = 13.10 ± 1.02 and 14.80 ± 0.74), 1,3-dimethoxy-2-methylanthraquinone (4, IC50 = 9.40 ± 3.51 and 28.40 ± 2.33), and 1,3-dihydroxy-2-methylanthraquinone (3, IC 50 = 25.60 ± 0.42 and 28.40 ± 0.79) also exhibited moderate cytotoxicity against MCF-7 and K-562 cancer cell lines, respectively. Other structurally related compounds like 1,3-dihydroxyanthraquinone (13a, IC50 = 19.70 ± 0.35 and 14.50 ± 1.28), 1,3-dimethoxyanthraquinone (13b, IC50 = 6.50 ± 0.66 and 5.90 ± 0.95) were also showed good cytotoxicity. The target compound damnacanthal (1) was found to be the most cytotoxic against the MCF-7 and K-562 cancer cell lines, with IC50 values of 3.80 ± 0.57 and 5.50 ± 1.26, respectively. The structures of all compounds were elucidated with the help of detailed spectroscopic techniques.
2-Methylanthraquinone derivatives as potential bioreductive alkylating agents
Lin,Teicher,Sartorelli
, p. 1237 - 1242 (2007/10/02)
Hypoxic cells of solid tumors are an obstacle to effective cancer therapy. Since hypoxic cells remote from the tumor blood supply may have a greater capacity for reductive reactions than well-oxygenated cells, the authors have prepared a series of anthraquinone prodrugs which may be capable of generating a reactive quinonemethide species following enzymatic reduction to the hydroquinone and loss of the substituent on the methylene group in the 2 position. The synthesized 2-methyl-substituted anthraquinone derivatives have first half-wave reduction potentials of -0.52 to -0.56 V at pH 7.0, which are the lowest oxidation-reduction potentials of quinone bioreductive alkylating agents synthesized by this laboratory to date. Tests of the cytotoxicity of these agents to oxygenated and chronically hypoxic EMT6 tumor cells in culture demonstrated that 2-(hydroxymethyl)anthraquinone, 2-[(N-methylcarbamyl)-methyl]anthraquinone, 2-[(p-toluenesulfonyl)oxy]methyl]anthraquinone, and 2-(methoxymethyl)anthraquinone were significantly more toxic to hypoxic cells than to their normally aerated counterparts. The findings demonstrate differences between various leaving groups in the 2 position for the expression of differential cytotoxicity.
