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Efficient Synthesis of Chromone and Flavonoid Derivatives with Diverse Heterocyclic Units
Author(s) -
Arai Midori A.,
Sato Mina,
Sawada Keisuke,
Hosoya Takahiro,
Ishibashi Masami
Publication year - 2008
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200800166
Subject(s) - chromone , flavones , chemistry , hela , combinatorial chemistry , flavonoid , cytotoxicity , molecule , aldol reaction , glycosylation , organic chemistry , stereochemistry , catalysis , in vitro , biochemistry , antioxidant , chromatography
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‐heterocyclic‐substituted 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.