天然紫草萘醌类化合物与苯胺和苯硫酚的亲核反应  

The Nucleophilic Reaction of P - Dimethylacrylalkannin with Aniline and Thiophenol

作　　者：黄志纾[1] 古练权[1] 车镇涛[2] 张敏[3] 邱光清[3] 

机构地区：[1]中山大学化学化工学院,广州510275 [2]香港科技大学化学系 [3]广东省药物研究所,广州510180

出　　处：《化学学报》2000年第8期1043-1049,共7页Acta Chimica Sinica

基　　金：国家自然科学基金(29872061);广东省自然科学基金(980320)资助课题;香港科技大学基金资助课题

摘　　要：研究了天然紫草萘醌类化合物β-二甲基丙烯酰阿卡宁在没有还原剂和有还原剂存在下与亲核试剂的反应,合成了七个新的萘茜类衍生物.比较了β-二甲基丙烯酰阿卡宁与合成衍生物的生物活性.Seven new naphthazarin derivatives were synthesized using the reactions of isolated β,β-dimethylacrylalkannin with aniline and thiophenol.β,β- dimethylacrylalkannin 1, a naphthazarin compound isolated from the root of Amebia euchroma, reacts with aniline to afford oxidative Michael addition products 2 and 3. Compound 1 reacts with aniline in the presence of NaBH, or with thiophenol to give the products 4,5, 6a ~ 6c. The 1H,13C NMR spectra of the products show that the hydrogen atom on 6 - C or 7 - C and the ester grorp on 1' - C of 1 are replaced by nucleophiles. It is concluded that nucleophiles add to the side chain (1'-C) by an reductive alkylation and to the quinone ring (6-C or 7-C) by an oxidative Michael addition. The cytotoxic activities of the natural and synthetic compounds were investigated.

关 键 词：萘茜衍生物 天然紫草萘醌 苯胺 苯硫酚 亲核反应 

分 类 号：O621.25[理学—有机化学]