A series of 1-benzo[1,3]dioxol-5-yl-indoles bearing 3-N-fused heteroaryl moieties have been designed based on literature reports of the activity of indoles against various cancer cell lines, synthesized via a Pd-catalyzed C-N cross-coupling, and evaluated for their anticancer activity against prostate (LNCaP), pancreatic (MIA PaCa-2), and acute lymphoblastic leukemia (CCRF-CEM) cancer cell lines. A detailed structure–activity relationship study culminated in the identification of 3-N-benzo[1,2,5]oxadiazole 17 and 3-N-2-methylquinoline 20, whose IC₅₀ values ranged from 328 to 644 nM against CCRF-CEM and MIA PaCa-2. Further mechanistic studies revealed that 20 caused cell cycle arrest at the S phase and induced apoptosis in CCRF-CEM cancer cells. These 1-benzo[1,3]dioxol-5-yl-3-N-fused heteroaryl indoles may serve as a template for further optimization to afford more active analogs and develop a comprehensive understanding of the structure–activity relationships of indole anticancer molecules.

一系列带有 3-N-稠合杂芳基部分的 1-benzo[1,3]dioxol-5-yl-indoles是基于通过 Pd催化合成的吲哚对各种癌细胞系活性的文献报道而设计的CN 交叉偶联，并评估它们对前列腺 (LNCaP)、胰腺 (MIA PaCa-2) 和急性淋巴细胞白血病 (CCRF-CEM) 癌细胞系的抗癌活性。详细的构效关系研究最终鉴定出 3- N-苯并[1,2,5]恶二唑17和 3 - N -2-甲基喹啉20，其 IC ₅₀针对 CCRF-CEM 和 MIA PaCa-2 的值范围为 328 至 644 nM。进一步的机制研究表明，20在 CCRF-CEM 癌细胞中导致细胞周期停滞在 S 期并诱导细胞凋亡。这些 1-benzo[1,3]dioxol-5-yl - 3 - N-稠合杂芳基吲哚可以作为进一步优化的模板，以提供更多活性类似物并全面了解吲哚抗癌分子的结构 - 活性关系.