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

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Abstract

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 situ 1H 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.

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

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Article information


Submitted
10 Jan 2020
Accepted
17 Mar 2020
First published
18 Mar 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

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

Z. Zhu, C. Chen, J. Jiang, Q. Zhang, Z. Du, S. Wei, X. Song, J. Tang, J. Lei, Z. Ke and Y. Zou, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00050G

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