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

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.