Efficient synthesis of chromone and flavonoid derivatives with diverse heterocyclic units.
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.
Arai
Midori A
MA
Graduate School of Pharmaceutical Sciences, Chiba University, Inage, Chiba (Japan). marai@p.chiba-u.ac.jp
Sato
Mina
M
Sawada
Keisuke
K
Hosoya
Takahiro
T
Ishibashi
Masami
M
D002867:Chromones / Q000138:chemical synthesis* / Q000737:chemistry; D005419:Flavonoids / Q000138:chemical synthesis* / Q000737:chemistry; D006367:HeLa Cells; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D006801:Humans; D020128:Inhibitory Concentration 50; D011725:Pyridines / Q000737:chemistry; D014407:Tumor Cells, Cultured
D002867:Chromones; D005419:Flavonoids; D006571:Heterocyclic Compounds; D011725:Pyridines