Department of Organic Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, Grunwaldzka Str. 6, 60-780 Poznan, Poland.
Org Biomol Chem. 2012 Mar 21;10(11):2201-5. doi: 10.1039/c2ob06923g. Epub 2012 Jan 5.
New A-ring or/and C-ring modified methyl oleanolate derivatives were prepared. New simple method of synthesis of 3,12-diketone (3) from methyl oleanonate (2) was worked out. The obtained new compounds were tested for cytotoxic activity on KB, MCF-7 and HeLa cell lines. The derivatives had acetoxy, oxo or hydroxyimino function at the C-3 position and in some cases oxo, hydroxyimino or acyloxyimino group at the C-12 position. Almost all of the compounds showed strong cytotoxic activity, higher than unchanged oleanolic acid. The most active substances turned out to be the derivatives with acyloxyimino function, especially 4 and 8d.
新型 A 环或/和 C 环修饰的甲基齐墩果酸衍生物被制备。从甲基齐墩果醇酸酯（2）合成 3,12-二酮（3）的新的简单方法被开发出来。所得到的新化合物在 KB、MCF-7 和 HeLa 细胞系上进行了细胞毒性活性测试。这些衍生物在 C-3 位具有乙酰氧基、氧代或羟亚氨基功能，在某些情况下在 C-12 位具有氧代、羟亚氨基或酰氧亚氨基基团。几乎所有的化合物都表现出很强的细胞毒性活性，高于不变的齐墩果酸。最活跃的物质是具有酰氧亚氨基功能的衍生物，特别是 4 和 8d。
