College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University, 85 Songdogwahak-ro, Yeonsu-gu, Incheon 21983, Republic of Korea.
Graduate Program of Industrial Pharmaceutical Science, Yonsei University, Incheon 21983, Republic of Korea.
J Org Chem. 2020 Aug 21;85(16):10994-11005. doi: 10.1021/acs.joc.0c01291. Epub 2020 Jul 30.
A highly efficient synthetic route to new quinone-indolizine hybrids was accomplished from quinones and -substituted pyrrole-2-carboxaldehydes via a domino Michael addition-aldol condensation-aromatization sequence through which the central pyridine ring was constructed in atom-economical and environment-friendly manner. Post modification of the resulting products was also demonstrated, enabling further expansion of this heterocyclic chemical space. Biological evaluation of the quinone-indolizine hybrids revealed potent anticancer effects in human prostate adenocarcinoma cells (PC-3) and oral adenosquamous carcinoma cells (CAL-27).
一种高效的合成新醌-吲哚嗪杂合体的方法是通过醌和取代的吡咯-2-甲醛醛经过多步迈克尔加成-羟醛缩合-芳构化反应完成的，其中通过原子经济和环保的方式构建了中心吡啶环。还展示了对所得产物的后修饰，从而进一步扩展了这个杂环化学空间。对醌-吲哚嗪杂合体的生物评估表明，它们对人前列腺腺癌细胞（PC-3）和口腔腺鳞癌细胞（CAL-27）具有很强的抗癌作用。
