Fu Liangfeng, Lin Qi-Xian, Onyango Evans O, Liby Karen T, Sporn Michael B, Gribble Gordon W
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.
Org Biomol Chem. 2017 Jul 19;15(28):6001-6005. doi: 10.1039/c7ob01420a.
We report the synthesis and biological activity of C-24 demethyl CDDO-Me 2 and the C-28 amide derivatives 3 and 4, which are analogues of the anti-inflammatory synthetic triterpenoid bardoxolone methyl (CDDO-Me) 1. Demethylation of the C-24 methyl group was accomplished via "abnormal Beckmann" rearrangement and subsequent ring A reformation. Amides 3 and 4 were found to be potent inhibitors of the production of the inflammatory mediator NO in vitro.
我们报道了C-24去甲基CDDO-Me 2以及C-28酰胺衍生物3和4的合成及其生物活性，它们是抗炎合成三萜类化合物巴多索隆甲酯（CDDO-Me）1的类似物。C-24甲基的去甲基化是通过“异常贝克曼”重排以及随后的A环重构来实现的。酰胺3和4在体外被发现是炎症介质NO产生的有效抑制剂。
