Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 3, Pages 682-686Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo01694f
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Funding
- Science and Technology Research Program of Chongqing Municipal Education Commission [CXQT19029, KJZD-M201801301]
- Science & Technology Department of Sichuan Province [2017FZ0084]
- Natural Science Foundation Project of CQ CSTSC [cstc2018jszx-cyzdX0023, cstc2021jcyj-bsh0233]
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A novel method for constructing naturally occurring spiroindolines with potential anti-cancer properties was developed, which can control the configuration of multiple chiral centers simultaneously.
A post-Ugi/diastereoselective cascade reaction was developed to construct naturally existing spiroindolines via a facile and metal-free one-pot protocol. During the construction, a new C-C bond was formed through a selective 5-exo-dig indole cyclization on the propiolamide; and a new C-N bond was diastereoselectively formed which controlled the configuration of three chiral centers simultaneously. Screening data of several difficult-to-inhibit cancer cell lines demonstrated that (+/-)-6d could strongly inhibit colon cell U87 proliferation with an IC50 value of 0.19 +/- 0.04 mu M. Taken together, our research provided a novel and robust protocol towards the synthesis of spiroindolines and revealed their potential application as anti-cancer agents in diverse human cancer cell lines.
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