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首页> 外文期刊>Chemistry: A European journal >New para-para stilbenophanes: Synthesis by mcmurry coupling, conformational analysis and inhibition of tubulin polymerisation
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New para-para stilbenophanes: Synthesis by mcmurry coupling, conformational analysis and inhibition of tubulin polymerisation

机译：新的对位对苯二酚：通过麦克默里偶联合成，构象分析和微管蛋白聚合反应的抑制

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摘要

The synthesis of a new family of methoxy-substituted [2.7]- and [2.8]paracyclophanes linked by 3-oxapentamethylene-1,5-dioxy and hexamethylene-1,6-dioxy bridges has been carried out by using the McMurry methodology. Related indole compounds were also synthesised. Olefin-to-diol ratios depended on the bridge length, the structure of the aromatic ring and the reaction conditions. Macrocyclisation, the methoxy substituents and the presence of a rigid indole moiety restricted the conformational equilibria, as observed by NMR spectroscopy and according to theoretical calculations. The synthesised compounds display micromolar tubulin polymerisation inhibitory activity. The conformational implications on the tubulin polymerisation inhibitory activity derived from the macrocyclisation when compared with combretastatins, closely related stilbenes, are also discussed. Flip-flop: McMurry coupling of dialdehydes was successfully used to complete the synthesis of macrocyclic stilbene analogues of combretastatins in variable yields (an example of which is depicted). These molecules have several exchanging conformations, as studied by NMR spectroscopy and theoretical calculations, and are the first macrocyclic inhibitors of tubulin polymerisation of their class.
机译：已经通过使用McMurry方法进行了由3-氧杂戊基-1，5-二氧基和六亚甲基-1，6-二氧基桥连接的新的甲氧基取代的[2.7]-和[2.8]对环环烷家族的合成。还合成了相关的吲哚化合物。烯烃与二醇的比例取决于桥的长度，芳环的结构和反应条件。通过NMR光谱法和根据理论计算观察到的大环化，甲氧基取代基和刚性吲哚部分的存在限制了构象平衡。合成的化合物显示微摩尔微管蛋白聚合抑制活性。还讨论了与康布雷他汀，密切相关的斯蒂芬苯甲醚相比，对源自大环化的微管蛋白聚合抑制活性的构象意义。人字拖：二醛的McMurry偶联成功地用于完成可变产量的康美他汀大环二苯乙烯类似物的合成（显示了一个例子）。通过NMR光谱学和理论计算，这些分子具有几种交换构象，并且是此类微管蛋白聚合反应的首个大环抑制剂。

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