Dipartimento di Scienze e Tecnologie Chimiche, Università di Roma Tor Vergata, Via della Ricerca Scientifica snc, 00133 Roma, Italy.
J Org Chem. 2012 Aug 17;77(16):6873-9. doi: 10.1021/jo300985x. Epub 2012 Aug 6.
A new class of pentacyclic diquinoid compounds has been synthesized with a facile one-pot reaction of two molecules of 2-hydroxynaphthoquinone and 1-bromoalkanes in the presence of ferrocene. These molecules were isolated as enol tautomers that exhibit intramolecular hydrogen bond and extended electronic conjugation as proved by the intense absorption spectrum with a broad band between 400 and 600 nm. The spectroscopic and electrochemical characterization of this new class of compounds has been performed. One of the synthesized diquinoid derivatives showed a significant cytotoxicity with IC(50) values of 25-50 μM against Cisplatin-Resistant SKOV3 and colon carcinoma SW480 cell lines. The results of our study provide a valuable tool to a one-pot synthesis of highly conjugated polyquinones, analogous to important biological systems, with significant antitumoral activity.
一类新型的五环二醌化合物已通过二分子 2-羟基萘醌和 1-溴代烷烃在二茂铁存在下的一锅法反应简便地合成。这些分子被分离为烯醇互变异构体，通过在 400 到 600nm 之间的宽波段的强吸收光谱证明了分子内氢键和扩展的电子共轭。对这一新类化合物进行了光谱和电化学特性分析。所合成的二醌衍生物之一对 Cisplatin-Resistant SKOV3 和结肠癌细胞 SW480 细胞系表现出显著的细胞毒性，IC（50）值为 25-50μM。我们的研究结果为一锅法合成与重要生物体系类似的高共轭聚醌提供了有价值的工具，具有显著的抗肿瘤活性。
