N-Iodosuccinimide-Promoted Synthesis of Indolo[3,2- c]quinolizines via Cascade Intramolecular C-N Bond Formation/Aromatization with 3-(1 H-Indol-3-yl)-2-(pyridin-2-yl)propanoates

Chen Chen; Xixiang Yang; Jiaxin Wang; Weiya Kong; Jianjun Chen; Xiaodong Tang

doi:10.1021/acs.joc.4c03039

N-Iodosuccinimide-Promoted Synthesis of Indolo[3,2- c]quinolizines via Cascade Intramolecular C-N Bond Formation/Aromatization with 3-(1 H-Indol-3-yl)-2-(pyridin-2-yl)propanoates

J Org Chem. 2025 Apr 25;90(16):5398-5406. doi: 10.1021/acs.joc.4c03039. Epub 2025 Apr 10.

Authors

Chen Chen¹, Xixiang Yang¹, Jiaxin Wang¹, Weiya Kong¹, Jianjun Chen¹, Xiaodong Tang¹

Affiliation

¹ Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Sciences, Southern Medical University, 1023 South Shatai Road, Baiyun District, Guangzhou 510515, People's Republic of China.

PMID: 40211452
DOI: 10.1021/acs.joc.4c03039

Abstract

An NIS-promoted cascade of intramolecular C-N bond formation/aromatization with 3-(1H-indol-3-yl)-2-(pyridin-2-yl)propanoates is described for synthesizing a polycyclic indole skeleton, indolo[3,2-c]quinolizine, as well as 1,9-dihydropyrazolo[4',3':5,6]pyrido[2,3-b]indole. The advantages of this protocol include accessible starting materials, mild conditions, simple operation, and good yields. Indolo[3,2-c]quinolizines exhibited good fluorescence properties and effective staining for live cells, targeting lysosomes and mitochondria. Additionally, the products showed significant antiproliferative activity against tumor cells in the MTT assay.