Structure-activity relationship study of 4′-O-methylgrynullarin derivatives for the development of novel anticancer agents based on anti-austerity strategy

Nguyen Ngoc Thanh Luan, Takuya Okada*, Ruka Arata, Lanke Prudhvi, Moe Miyaguchi, Yuri Kodama, Suresh Awale*, Naoki Toyooka

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

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 languageEnglish
Article number132931
JournalTetrahedron
Volume122
DOIs
StatePublished - 2022/09/10

Keywords

  • 4′-O-Methylgrynullarin
  • Anti-austerity strategy
  • Anticancer
  • Isoflavone
  • Structure-activity relationship

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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