Department of Pharmaceutical and Toxicological Chemistry, University of Naples Federico II, Via D. Montesano 49, I-80131 Naples, Italy.
Bioorg Med Chem. 2010 Jun 15;18(12):4328-37. doi: 10.1016/j.bmc.2010.04.079. Epub 2010 Apr 29.
Based on the spirotryprostatin-A structure, we designed, synthesized, and evaluated different series of compounds belonging to the diketopiperazine structural class as potential cell cycle modulators and cytotoxic agents. Starting from the spirooxoindolthiazolidine scaffold, amide coupling with Pro derivatives and intramolecular cyclization reactions are suitable synthetic methods to generate chemically diverse diketopiperazine system, such as hexahydropyrrolo[1,2-a][1,3]thiazolo[3,2-d]pyrazine-5,10-dione (structure I), hexahydropyrrolo[1,2-a] [1,3]thiazolo[3,4-d]pyrazine-5,10-dione (structure II) and spiroindol-2-one[3,3']hexahydro-5,10H-pyrrolo[1,2-a][1,3]thiazolo[3,4-d]pyrazine-5,10-dione (structure III). Some of these compounds, especially those who belong to the series I and II, showed interesting cytotoxic activity.
基于螺环三并苯-A 的结构，我们设计、合成并评估了不同系列的二酮哌嗪类化合物，它们作为潜在的细胞周期调节剂和细胞毒性剂。从螺环氧吲哚噻唑烷骨架出发，酰胺偶联与 Pro 衍生物和分子内环化反应是生成化学多样性二酮哌嗪体系的合适合成方法，例如六氢吡咯并[1,2-a][1,3]噻唑并[3,2-d]吡嗪-5,10-二酮（结构 I）、六氢吡咯并[1,2-a][1,3]噻唑并[3,4-d]吡嗪-5,10-二酮（结构 II）和螺吲哚-2-酮[3,3']六氢-5,10H-吡咯并[1,2-a][1,3]噻唑并[3,4-d]吡嗪-5,10-二酮（结构 III）。这些化合物中的一些，特别是属于 I 类和 II 类的化合物，表现出有趣的细胞毒性活性。
