二元酸茄呢醇乙酰葡萄糖二酯的合成及其生物活性

Synthesis and Biological Activity of Solanesyl Glucosyl Dibasic Acid Esters

以茄呢醇为原料 ,与 7种不同的酸酐反应制得相应的二元酸茄呢醇单酯 (2 ) ,后者在四丁基溴化铵作相转移催化剂的条件下与α D 1 溴代四乙酰葡萄糖反应生成对应的二元酸茄呢醇乙酰葡萄糖二酯 (3) ,该相转移催化法具有反应条件温和 ,后处理简单和立体选择性强的优点。制得的 14个化合物均为新化合物 ,其结构经元素分析、IR、1 HNMR和MS确证。初步测试了 2a、2e、2g 3种化合物和 7种化合物 3a～ 3g对 3种人癌细胞的体外活性。结果发现 ,3e对人口腔上皮癌细胞有较好的体外抑制活性 。

Solanesol was reacted with seven dibasic acid anhydrides to give corresponding monosolanesyl dibasic acid esters 2, which were reacted with 2,3,4,6 tetra O acetyl α D glucopyranosyl bromide to give corresponding solanesyl glucosyl dibasic esters 3, using tetrabutyl ammonium bromide as a phase transfer catalyst .The method has advantages of mild reaction condition, easy seperation and high stereospecificity of the products. The structures of all the compounds 2 and 3 were confirmed by IR, NMR, MS and elemental analysis. Preliminary in vitro biological activity tests of three compounds of 2 and seven compounds of 3 against three kinds of human cancer cells showed that 3e has moderate inhibitory activity(～70%) on KB cells, and the other compounds have only low inhibitory ratios.