State Key Laboratory of Quality Research in Chinese Medicine, Macau Institute for Applied Research in Medicine and Health, Guangdong-Hong Kong-Macao Joint Laboratory of Respiratory Infectious Disease, Macau University of Science and Technology, Taipa, Macau 999078, People's Republic of China.
School of Chemistry and Chemical Engineering, Linyi University, Linyi, Shandong 276000, People's Republic of China.
J Org Chem. 2022 Jun 17;87(12):7955-7967. doi: 10.1021/acs.joc.2c00598. Epub 2022 Jun 2.
An efficient TfOH-catalyzed cascade C-H/N-H annulation of indole-2-carboxamides with benzoquinones has been developed for the synthesis of tetracyclic indolo[2,3-]quinolinones. This reaction exhibits excellent chemo-/regioselectivity, achieving functionalization of the C-3 of indole and N-H of the amide moiety to form the new C-C and C-N bonds. Various expected products were synthesized from readily available starting materials in good to high yields with a wide substrate scope and good functional group tolerance. Among all synthetic products, showed the most potent cytotoxicity toward the 4T1 cancer cell line with an IC value of 0.62 ± 0.05 μM. study demonstrated that remarkably suppressed 4T1 xenograft tumor growth without body weight loss.
一种高效的 TfOH 催化的吲哚-2-甲酰胺与苯醌的级联 C-H/N-H 环化反应已被开发用于合成四环吲哚并[2,3-]喹啉酮。该反应表现出优异的化学/区域选择性，实现了吲哚 C-3 和酰胺部分的 N-H 的官能化，形成了新的 C-C 和 C-N 键。各种预期的产物可以从易得的起始原料以良好至高产率合成，具有广泛的底物范围和良好的官能团耐受性。在所合成的产物中，化合物 对 4T1 癌细胞系表现出最强的细胞毒性，IC 值为 0.62±0.05 μM。研究表明，化合物 显著抑制了 4T1 异种移植肿瘤的生长，而没有体重减轻。
