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

Abstract

Abstract: A facile synthetic route to the natural products suffrutines A (1a), B (1b) and their N-fused analogues (2a, 2b) has been accomplished starting from pyrrole in 8 steps. Their structures were elucidated by a series of NMR spectra and the single-crystal X-ray crystallography. The in-situ 1HNMR monitoring experiments showed the interconversion properties of four suffrutines isomers and a stability order of 1a (E, E) > 1b (Z, E) > 1d (Z, Z) > 1c (E, Z) in solution state under ambient conditions. DFT calculations further clarified the tautomerization results. Preliminary biological tests showed that 1’-aza-suffrutines B (2b) was the most potent in cytotoxic study (MCF-7, IC50 = 7.13 μM), while 1’-aza-suffrutines A (2a) was 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.

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Article information


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

Org. Chem. Front., 2020, Accepted Manuscript
Article type
Research Article

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

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

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