One-pot synthesis of natural-product inspired spiroindolines with anti-cancer activities
Literature Information
Publication Date
2021-12-15
DOI
10.1039/D1QO01694F
Impact Factor
5.281
Authors
Shi-Qiang Li, Liu-Jun He, Ming Zhang, Dian-Yong Tang, Hong-yu Li, Zhong-Zhu Chen, Zhi-Gang Xu
View Original
Abstract
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
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
Recommended Compounds
2-(4,4-Difluorobutyl)-1H-isoindole-1,3(2H)-dione
CAS Number:
1265341-14-7
Molecular Formula:
C12H11F2NO2
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