Publication: Copper-catalyzed synthesis and anticancer activity evaluation of indolo[1,2-a]quinoline derivatives
Issued Date
2021-10-12
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ISSN
18733581
00404039
00404039
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2-s2.0-85114674977
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Mahidol University
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SCOPUS
Bibliographic Citation
Tetrahedron Letters. Vol.82, (2021)
Suggested Citation
Adisak Thanetchaiyakup, Suparerk Borwornpinyo, Hassayaporn Rattanarat, Phongthon Kanjanasirirat, Kedchin Jearawuttanakul, Sawinee Seemakhan, Nutthawat Chuanopparat, Paiboon Ngernmeesri Copper-catalyzed synthesis and anticancer activity evaluation of indolo[1,2-a]quinoline derivatives. Tetrahedron Letters. Vol.82, (2021). doi:10.1016/j.tetlet.2021.153365 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/75996
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Title
Copper-catalyzed synthesis and anticancer activity evaluation of indolo[1,2-a]quinoline derivatives
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Abstract
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 μM and in the range of 6.21–46.91 μM, respectively.