- Synthesis, anti-cancer and anti-inflammatory activity of novel 2-substituted isoflavenes
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Fifteen novel 2-substituted isoflavenes were synthesised via nucleophilic addition to isoflavylium salts. Twelve of the newly synthesised isoflavenes, along with the unsubstituted parent isoflavene, were tested in cell viability assays against the SHEP neuroblastoma and MDA-MB-231 breast adenocarcinoma cell lines. While the 2-substituted isoflavenes displayed a range of anti-proliferative activities, in most cases they were less active that the unsubstituted isoflavene (IC50= 9.9 μM vs SHEP; IC50= 33 μM vs MDA-MB-231). However, compound 7f, derived from the reaction between isoflavylium salt 5 and para-methoxyacetophenone, showed improved anti-proliferative activity against breast cancer cells (IC50= 7.6 μM). Furthermore, compound 7f, as well as analogues 7a, 7c, 11d and 14, inhibited the production of interleukin-6 in LPS-activated RAW 264.7 cells.
- Eiffe, Eleanor,Pasquier, Eddy,Kavallaris, Maria,Herbert, Cristan,Black, David St.C.,Kumar, Naresh
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- A facile approach to 2-substituted isoflav-3-enes via isoflavylium salts
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A compact and regioselective approach to 2-substituted isoflav-3-enes based on a preformed 2-unsubstituted isoflavene is described. Isoflavene oxidation by hydride ion abstraction to the corresponding isoflavylium salt using trityl hexafluorophosphate fol
- Faragalla, Jane,Heaton, Andrew,Griffith, Renate,Bremner, John B.
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p. 306 - 309
(2009/06/25)
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- Production of isoflavone derivatives
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Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.
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Page/Page column 10
(2008/06/13)
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- A Synthesis of Hydroxylated Isoflavylium Salts and Their Reduction Products
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Phloroglucinol reacts with arylmalondialdehydes in the presence of hydrochloric acid to form 5,7-dihydroxyisoflavylium salts.Reduction of these salts can be utilized to form isoflav-2-enes, isoflav-3-enes or isoflavans.
- Liepa, Andris J.
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p. 2647 - 2655
(2007/10/02)
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