Synthesis and cytotoxicity study of alkannin derivatives.
Alkannin derivatives (3-19) were prepared through the reaction of beta,beta-dimethylacrylalkannin (1), the most abundant isohexenylnaphthazarin isolated from the roots of Arnebia euchroma, with different types of nucleophiles such as amines and thiols in the absence or presence of a reducing agent. The cytotoxicities of 1-8, 10-14 and 19 against four human carcinoma cell line (GLC-82, CNE2, Bel-7402, K-562) were found to be markedly higher than that of the naturally occurring beta,beta-dimethylacrylalkannin (1) and acetylalkannin (2). This study also shed light on the understanding of the biological activities in terms of the chemical reactivity of alkannins.
Huang
Zhi-Shu
ZS
School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510080, China. huangzhishu@hotmail.com
Wu
Hai-Qiang
HQ
Duan
Zhi-Fang
ZF
Xie
Bing-Fen
BF
Liu
Zong-Chao
ZC
Feng
Gong-Kan
GK
Gu
Lian-Quan
LQ
Chan
Albert S C
AS
Li
Yue-Ming
YM
D028082:Boraginaceae / Q000737:chemistry; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D009285:Naphthoquinones; C018204:alkannin; C005503:naphthazarin