Abstract
2-Aryl/alkylbenzofurans, which constitute an important subclass of naturally occurring lignans and neolignans, have attracted extensive synthetic efforts due to their useful biological activities and significant pharmacological potential. Herein, we report a general and efficient approach to divergent 2-arylbenzofurans through a one-pot synthesis of versatile 2-bromobenzofurans as key intermediates. Using this approach, the first total synthesis of a series of trisubstituted and tetrasubstituted benzofurans bearing the hydroxyethyl unit, including the natural compounds isolated from Lavandula agustifolia (1-3) and their non-natural derivatives (4-8), was accomplished. We also report a modified synthesis of ailanthoidol, homoegonol, and egonol that enables the divergent synthesis of their derivatives for future exploration. Among these, the representative phenolic natural compound 2 and its derivatives 7 and 5 induced apoptotic cell death related poly(ADP-ribose) polymerase (PARP) cleavage in MCF74, A549, PC3, HepG2, and Hep3B cancer cell lines. Additionally, the tumor suppressor protein p53 was also induced in p53 wild type cancer cells.
Original language | English |
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Pages (from-to) | 3354-3362 |
Number of pages | 9 |
Journal | Journal of Natural Products |
Volume | 83 |
Issue number | 11 |
DOIs | |
Publication status | Published - 2020 Nov 25 |
Bibliographical note
Funding Information:This study was funded with a National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (NRF 2018R1A5A2023127) and National Cancer Center Research Grants [1810030 to K.K. and J.-W.P.].
Publisher Copyright:
© 2020 American Chemical Society. All rights reserved.
ASJC Scopus subject areas
- Analytical Chemistry
- Molecular Medicine
- Pharmacology
- Pharmaceutical Science
- Drug Discovery
- Complementary and alternative medicine
- Organic Chemistry