One-pot synthesis of natural-product inspired spiroindolines with anti-cancer activities

文献情報

出版日 2021-12-15

DOI 10.1039/D1QO01694F

インパクトファクター 5.281

著者

Shi-Qiang Li, Liu-Jun He, Ming Zhang, Dian-Yong Tang, Hong-yu Li, Zhong-Zhu Chen, Zhi-Gang Xu

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要旨

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 μM. 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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

One-pot synthesis of natural-product inspired spiroindolines with anti-cancer activities

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