Efficient synthesis of chromone and flavonoid derivatives with diverse heterocyclic units

Midori A. Arai, Mina Sato, Keisuke Sawada, Takahiro Hosoya, Masami Ishibashi

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

Chromones and flavonoids are important bioactive compounds. We envisioned that new heterocyclic-substituted chromones or flavonoids might act as new bioactive compounds. To obtain diverse molecules, we developed an efficient one-pot synthesis by Michael aldol reaction of chromone and flavonoid derivatives bearing heterocyclic units. The 2,3-heterocyclicsubstituted chromones were obtained in one step. Moreover, the use of substituted benzaldehydes and subsequent addition of heterocyclic aldehydes gave 3-pyridyl-substituted flavones. We also examined these one-pot reactions in the solid phase. To introduce an additional point of diversity into the molecules, Suzuki-Miyaura coupling was performed. Furthermore, we identified the cytotoxicity of the synthesized compounds against cancer cells (PANC1 and HeLa cells). Several compounds were cytotoxic to these cancer cells.

Original languageEnglish
Pages (from-to)2056-2064
Number of pages9
JournalChemistry - An Asian Journal
Volume3
Issue number12
DOIs
Publication statusPublished - 2008 Dec 1
Externally publishedYes

Keywords

  • Chromones
  • Flavonoids
  • Michael aldol
  • One-pot synthesis
  • Pyridine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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