<i>N</i>-Iodosuccinimide-Promoted Synthesis of Indolo[3,2-<i>c</i>]quinolizines via Cascade Intramolecular C–N Bond Formation/Aromatization with 3-(1<i>H</i>-Indol-3-yl)-2-(pyridin-2-yl)propanoates
An NIS-promoted cascade of intramolecular C-N bond formation/aromatization with 3-(1<i>H</i>-indol-3-yl)-2-(pyridin-2-yl)propanoates is described for synthesizing a polycyclic indole skeleton, indolo[3,2-<i>c</i>]quinolizine, as well as 1,9-dihydropyrazolo[4',3':5,6]pyrido[2,3-<i>b</i>]indole. The advantages of this protocol include accessible starting materials, mild conditions, simple operation, and good yields. Indolo[3,2-<i>c</i>]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.
Authors
- Xiaodong Tang (ORCID: https://orcid.org/0000-0002-0051-105X)
- Jiaxin Wang (ORCID: https://orcid.org/0000-0001-7033-7854)
- Jianjun Chen (ORCID: https://orcid.org/0000-0001-5668-6572)
- Chen Chen (ORCID: https://orcid.org/0000-0002-5388-9611)
- Xixiang Yang (ORCID: https://orcid.org/0000-0003-4109-9505)
- Weiya Kong
Institutions
- Southern Medical University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-04-11
- DOI
- https://doi.org/10.1021/acs.joc.4c03039
- Primary Topic
- Synthesis and bioactivity of alkaloids
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Basic and Applied Basic Research Foundation of Guangdong Province