Graduate School of Pharmacy Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan.
Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan.
Eur J Med Chem. 2017 Aug 18;136:1-13. doi: 10.1016/j.ejmech.2017.04.071. Epub 2017 Apr 28.
We developed a concise protocol for the synthesis of ellipticine quinone from the appropriate 3-iodoindole-2-carbaldehydes in four steps. The key step is the construction of carbazole-1,4-quinone through tandem Ring-Closing Metathesis (RCM) and dehydrogenation under oxygen atmosphere. Therefore, the ellipticine quinone analogs possessing substitution at the 8- and/or 9-positions were synthesized using this method. In total, 14 compounds were evaluated for antiproliferative activity against HCT-116 and HL-60 cell lines; 9-nitroellipticine quinone was found to have superior activity compared to calothrixin B.
我们开发了一种从适当的 3-碘吲哚-2-醛出发，经四步反应合成椭圆素醌的简洁方案。关键步骤是在氧气氛围下通过串联的闭环复分解（RCM）和脱氢反应构建咔唑-1,4-醌。因此，使用该方法合成了在 8-和/或 9-位取代的椭圆素醌类似物。总共评估了 14 种化合物对 HCT-116 和 HL-60 细胞系的抗增殖活性；发现 9-硝基椭圆素醌比 calothrixin B 具有更好的活性。
