天然产物研究与开发2017，Vol.29Issue(9)：1464-1469,1567,7.DOI:10.16333/j.1001-6880.2017.9.002
葡萄糖氨基醌类的合成
Synthesis on Glucoseamino Quinones
摘要
Abstract
Because the general small quinone molecules are fat-soluble compounds.They are insoluble in water and cannot be directly intravenous administration.Thus their clinical application is limited.To enhance the quinone molecular polarity and solubility,improving the biological structure of the mother,the quinones mother ring were tried to introduce hydrophilic glucose amino.The nucleophilic addition reaction of the aromatic ring with different structure types and the effect of glucosamine on the ortho and para quinones were investigated respectively.Tetrachloroquinone,2,3-dichloro-1,4-naphthoquinone,1,4-naphthoquinone,alizarin,alizarin red and glucosamine hydrochloride were used as a raw material,morphine and furfurylamine were used as auxiliary material.First,glucosamine was reacted with an equimolar amount of quinones to obtain mono-glucosamino substituted trichlorobenzoquinone (b).Then (b) was reacted with an equimolar amount of furfuryl amine or morpholine to produce the glucosaminobenzoquinones (d) and (e) with a heterocyclic structure.The reaction between an equimolar amount of glucosamine and 2,3-dichloro-1,4-naphthoquinone can generate a single glucosamino-substituted naphthoquinone (i).Compounds (b),(k),(m) and (n) can be produced by the addition-oxidation method of reaction between an equimolar amount of glucosamine and 1,4-naphthoquinone or alizarin or alizarin red.The yield of addition-oxidation method is higher than that of haloquinone method,and the separation operation is relatively simple.All products were characterized by IR,UV,NMR and MS.关键词
苯醌/萘醌/蒽醌/氨基葡萄糖/合成Key words
benzoquinone/naphthoquinone/anthraquinone/glucosamine/synthesis分类
化学化工引用本文复制引用
王建,许烨,刘玮炜,陶传洲,盛婷,丁红伟,孙威..葡萄糖氨基醌类的合成[J].天然产物研究与开发,2017,29(9):1464-1469,1567,7.基金项目
江苏省优势学科建设工程资助(BK20130404) （BK20130404）
海洋公益性行业科研专项经费项目(201505023) （201505023）
连云港市科技攻关计划-农业攻关(CN1401) （CN1401）
江苏省环境材料与环境工程重点实验室开放研究课题(K12029) （K12029）
