title: Synthesis and cytotoxicity study of alkannin derivatives.
abstract: 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.
authors.affiliation: School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou 510080, China. huangzhishu@hotmail.com
authors.forename: Zhi-Shu
authors.initials: ZS
authors.lastname: Huang
authors.forename: Hai-Qiang
authors.initials: HQ
authors.lastname: Wu
authors.forename: Zhi-Fang
authors.initials: ZF
authors.lastname: Duan
authors.forename: Bing-Fen
authors.initials: BF
authors.lastname: Xie
authors.forename: Zong-Chao
authors.initials: ZC
authors.lastname: Liu
authors.forename: Gong-Kan
authors.initials: GK
authors.lastname: Feng
authors.forename: Lian-Quan
authors.initials: LQ
authors.lastname: Gu
authors.forename: Albert S C
authors.initials: AS
authors.lastname: Chan
authors.forename: Yue-Ming
authors.initials: YM
authors.lastname: Li
mesh_terms: 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
chemical_list: D009285:Naphthoquinones; C018204:alkannin; C005503:naphthazarin