新型胍基葡萄糖苷的合成及生物活性  

Synthesis and Biological Activities of Novel Guanidinoglucosides

作　　者：连召斌[1] 田晓红[1] 曹玲华[1] 

机构地区：[1]新疆大学化学化工学院,乌鲁木齐830046

出　　处：《高等学校化学学报》2007年第7期1297-1303,共7页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:29962002;20462006)资助

摘　　要：将2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基异硫氰酸酯(1)与2-氨基-4/6-取代-苯并噻唑(2a～2e)反应,生成糖基硫脲衍生物(3a～3e),再在伯胺存在下经氯化汞脱硫,得到一系列新的多乙酰基胍基糖苷类化合物(4a～4d,5a～5d,6a～6d,7a～7d),糖基的保护基团在甲醇钠/甲醇条件下脱除.所有新化合物的结构均经IR,1H NMR,MS谱和元素分析证实,所得产物均为β-构型.生物活性测试结果表明,化合物4c,6c,8b,8c等对HIV-1蛋白酶表现出了较高的抑制活性;化合物7c具有抗流感乙型病毒活性;化合物5e,7c,7d等对血管紧张素转化酶具有抑制活性.The reaction of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 1 with 2-amino-4/6-substituted benzothiazoles 2a--2b gave glucosylthioureas（3a-3b） , which then reacted with alkyl/aryl amine in the presence of HgCl2 to afford a series of new poly-acetyl guanidinoglucosides（4a-4d, 5a-5d, 6a-6d and 7a-7d）. Deacetylation of glycosyl was carried in the CH3OH/CH3ONa solution. The structures of the new compounds were established on the basis of elemental analyses, IR,^1H NMR and mass spectral data and all compounds took β-configuration. The biological activities of these compounds have been evaluated. Com- pounds 4c, 6c, 8b and 8c showed anti-HIV-1 PR activity, compound 7c showed anti-influenza activity and compounds 5e, 7c and 7d showed inhibitory activity against angiotensin-converting enzyme（ACE） activity .

关 键 词：糖基异硫氰酸酯 糖基硫脲 胍基糖苷 生物活性 

分 类 号：O626.27[理学—有机化学]