Abstract
4′-O-Methylgrynullarin 1 and its derivatives 2–4 showed preferential cytotoxicity under nutrient-deprived conditions without cytotoxicity under normal-nutrient conditions, indicating that its derivatives might have the potential to lead to novel anti-cancer agents based on anti-austerity strategy. The divergent synthesis of 4′-O-methylgrynullarin derivatives using the Suzuki-Miyaura coupling reaction as a key step and the evaluation of the synthesized derivatives revealed a clear structure-activity relationship. We found that the 6-prenyl moiety and 7-phenolic hydroxy group on the isoflavone skeleton are essential for preferential cytotoxicity, and that even if the substituent groups on C-ring are simpler than those in 1–4, cytotoxicity is maintained to some extent.
Original language | English |
---|---|
Article number | 132931 |
Journal | Tetrahedron |
Volume | 122 |
DOIs | |
State | Published - 2022/09/10 |
Keywords
- 4′-O-Methylgrynullarin
- Anti-austerity strategy
- Anticancer
- Isoflavone
- Structure-activity relationship
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry