Journal
TETRAHEDRON LETTERS
Volume 82, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2021.153365
Keywords
One-pot synthesis; Indolo[1,2-a]quinoline; Knoevenagel condensation; Ullmann-type reaction
Categories
Funding
- Thailand Research Fund [DBG5480018]
- Royal Golden Jubilee Advanced Program under the Thailand Research Fund [RAP61K0005]
- Kasetsart University Research and Development Institute (KURDI)
- Center of Excellence for Innovation in Chemistry (PERCH-CIC), Ministry of Higher Education, Science, Research and Innovation
- Faculty of Science, Kasetsart University
- Department of Chemistry
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A new synthesis method has been developed for substituted indolo[1,2-a]quinolines with high yields, which exhibit activity against breast cancer and colorectal cancer cells.
A simple and effective one-pot synthesis of substituted indolo[1,2-a]quinolines has been developed. The desired products were obtained in up to 98% yield when substituted 2-methyindoles were treated with 2-iodobenzaldehyde in the presence of Cs2CO3, CuI and L-proline. Our mechanistic study confirmed that the reaction sequence involved an intermolecular Knoevenagel reaction followed by an intramolecular Ullmann-type coupling reaction. Moreover, some of the synthesized compounds were found to be active against human breast (MCF-7) and colorectal (HCT-116) cancer cells with IC50 values of 27.96 mu M and in the range of 6.21-46.91 mu M, respectively. (C) 2021 Elsevier Ltd. All rights reserved.
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