Stereoselective synthesis and cytotoxicity of a cancer chemopreventive naphthoquinone from Tabebuia avellanedae.
Stereoselective synthesis of 1, one of biologically active naphthoquinones from a Brazilian traditional medicine Tabebuia avellanedae, was achieved by utilizing Noyori reduction as a key step. Compound 1 displayed potent cytotoxicity against several human tumor cell lines, whereas it showed lower cytotoxicity against some human normal cell lines compared with that of mitomycin. On the other hand, its enantiomer was less active toward the tumor cell lines than 1.
Yamashita
Mitsuaki
M
Faculty of Pharmacy, Takasaki University of Health and Welfare, Nakaorui-machi, Takasaki 370-0033, Japan.
Kaneko
Masafumi
M
Iida
Akira
A
Tokuda
Harukuni
H
Nishimura
Katsumi
K
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000633:toxicity*; D045744:Cell Line, Tumor; D006801:Humans; D008968:Molecular Conformation; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000633:toxicity*; D010936:Plant Extracts / Q000138:chemical synthesis / Q000633:toxicity; D029663:Tabebuia
D000972:Antineoplastic Agents, Phytogenic; D009285:Naphthoquinones; D010936:Plant Extracts