Laboratoire de Pharmacognosie, (Univ. Paris-Sud 11, BIOCIS, UMR-8076 CNRS), Faculté de Pharmacie, av. J.B. Clément, 92296 Châtenay-Malabry Cedex, France.
Bioorg Med Chem. 2012 Feb 1;20(3):1231-9. doi: 10.1016/j.bmc.2011.12.038. Epub 2011 Dec 30.
Analogs of 3'-amino-5-hydroxy-3,6,7,8,4'-pentamethoxy-flavone, a strongly cytotoxic and antimitotic semisynthetic flavone, were synthesized in the aurone, isoflavone and isoflavanone series. Comparison of the biological activity of these new compounds with the reference showed a potent cytotoxicity only in the flavone series. Influence of the hydroxy group (at C-5 in flavones, at C-4 in aurones) on the cytotoxicity, known to be favorable in flavones, was found to be detrimental in aurones. This observation was related to the hydrogen bonding formed with the carbonyl group, strong in the flavones, but of weak intensity in the aurones.
3'-氨基-5-羟基-3,6,7,8,4'-五甲氧基黄酮类似物是一种具有强细胞毒性和抗有丝分裂作用的半合成黄酮，其在橙酮、异黄酮和异黄烷酮系列中被合成。将这些新化合物与参比物的生物活性进行比较，结果表明仅在黄酮系列中具有很强的细胞毒性。已知在黄酮中有利的羟基（在黄酮中为 C-5，在橙酮中为 C-4）对细胞毒性的影响在橙酮中是有害的。这一观察结果与与羰基形成的氢键有关，在黄酮中氢键很强，但在橙酮中氢键强度较弱。
