Synthesis and biological evaluation of suffrutines A, B and their N-fused analogues

文献情報

出版日 2020-03-18

DOI 10.1039/D0QO00050G

インパクトファクター 5.281

著者

Zefeng Zhu, Chun Chen, Jingxing Jiang, Qianzhong Zhang, Zhibo Du, Shuxian Wei, Xianheng Song, Jie Tang, Jinping Lei, Zhuofeng Ke, Yong Zou

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要旨

A facile synthetic route to the natural products suffrutines A (1a), B (1b) and their N-fused analogues (2a and 2b) has been accomplished starting from pyrrole in 8 steps. Their structures were elucidated by a series of NMR spectra and single crystal X-ray crystallography. The in situ1H NMR monitoring experiments showed the interconversion properties of the four isomers of suffrutines and their stability order 1a (E, E) > 1b (Z, E) > 1d (Z, Z) > 1c (E, Z) in the solution state under ambient conditions. DFT calculations further confirmed the tautomerization results. The preliminary biological test results showed that 1′-aza-suffrutines B (2b) was the most potent in cytotoxic study (MCF-7, IC50 = 7.31 μM), while 1′-aza-suffrutines A (2a) was the most active in a 14-day colony formation assay. In addition, 2a was proved to be a cancer cell apoptosis inducer in annexin V-FITC/PI dual staining tests.

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