含吖啶基的单环β-内酰胺及噻唑啉酮衍生物的合成及其生物活性  

Synthesis and Bioactivity of Monocyclic β-Lactams and 4-Thiazolidinones Derivatives Containing Acridinyl

作　　者：力瓦依丁.买合苏提 穆赫塔尔.伊米尔艾山 麦麦提依明.马合木提 萨特瓦尔迪.赫力力 刘华君[2] 

机构地区：[1]新疆大学化学与化工学院,乌鲁木齐830046 [2]新疆农业科学院经济作物研究所,乌鲁木齐830091

出　　处：《有机化学》2014年第6期1235-1239,共5页Chinese Journal of Organic Chemistry

基　　金：新疆维吾尔自治区自然科学基金(No.200421126);国家自然科学基金(No.21062019)资助项目~~

摘　　要：9-吖啶基甲醛芳亚胺席夫碱分别与氯乙酰氯、苄氧乙酰氯在三乙胺作用下产生的烯酮发生[2＋2]环加成反应和巯基乙酸的合环反应,合成了9个1-芳基-3-取代-4-（9-吖啶基）-氮杂环丁-2-酮衍生物L1～L6和2-（9-吖啶基）-3-芳基-1,3-噻唑烷-4-酮衍生物T1～T3,对所合成的化合物进行了体外抗癌活性和白细胞共同抗原活性筛选.结构表明,当样品浓度为10μmol/L时,化合物L4对肿瘤细胞HL-60（Leucocythemia人白血病细胞）生长的抑制率为79.4%.当样品浓度为20μg/mL时,化合物L5,L6和T3对细胞分裂周期磷酸酯酶Cdc25B（Cell division cycle 25B phosphatase）的抑制率分别为80.64%,99.75%和99.34%.当样品浓度为20μmol/mL时,化合物L6和T3对CD45（leukocyte common antigen,LCA白细胞共同抗原）蛋白酪氨酸磷酸酶A的抑制率分别为86.12%和91.03%.在此基础上,初步讨论了该类化合物的构效关系.In this paper, 1-aryl-3-substituted-4-（9-acridinyl）azetidin-2-one derivatives L1 ～ L6 and 2-（9-acridinyl）-3-aryl-1,3-thiazolidin-4-one derivatives T1～T3 were synthesized through [2＋2] cycloaddition reaction and cyclocondensation reaction of N-（p-substitutedaryl）-C-（9-acridinyl）formaldimines Schiff base with ketene, which in situ generated from chloroacetyl chloride and benzyloxyacetyl chloride in the presence of triethylamine, and mercaptoacetic acid. The synthesized compounds have also been screened in vitro anticancer activities and the leukocyte common antigen activities. The results showed that the inhibitory activity of compound L4 is 79.4% on human tumor cell HL-60（Leucocythemia）, at the test concentration of 10 μmol/L. The inhibitory activities of compounds L5, L6 and T3 on Cdc25B（Cell division cycle 25B） phosphatase are 80.64%, 99.75% and 99.34% at the test concentration of 20 μg/mL, respectively. The inhibitory activities of compounds L6 and T3 on CD45（leukocyte common antigen, LCA） protein tyrosine phosphatase A are 86.12% and 91.03% at the test concentration of 20 μmol/mL, respectively. The structure-activity relationship of these compounds was investigated on the bases of bioassay experimental results of these compounds.

关 键 词：吖啶基 Β-内酰胺 噻唑啉酮 合成 生物活性 

分 类 号：O621.3[理学—有机化学]