新型2-苯并噻唑磺酰脲氨基酸及其甲酯衍生物的合成与抗肿瘤活性  

Synthesis and Antitumor Activities of 2-Benzothiazolesulfonylureido Amino Acids and Their Methyl Esters

作　　者：田静[1] 常霄巍 巴俊杰[1] 

机构地区：[1]内蒙古医科大学药学院,内蒙古呼和浩特010110

出　　处：《合成化学》2016年第5期393-397,401,共6页Chinese Journal of Synthetic Chemistry

基　　金：内蒙古自治区自然科学基金资助项目(2013MS1210);内蒙古自治区高等学校科学研究项目(NJZY13427)

摘　　要：以2-巯基苯并噻唑为原料,经弱氧化和氨化制得2-苯并噻唑次磺酰胺(2);2经高锰酸钾氧化制得2-苯并噻唑磺酰胺(3);3与氯甲酸乙酯反应制得2-苯并噻唑磺酰胺甲酸乙酯(4);4与L-氨基酸甲酯反应制得一系列2-苯并噻唑磺酰脲氨基酸甲酯(6a^6j);6经水解合成了10个新型的2-苯并噻唑磺酰脲氨基酸(7a^7j),其结构经~1H NMR,IR和ESI-MS表征。并研究了6和7对Cdc25B的抑制活性。结果表明:在用药浓度为20μg·m L^(-1)时,6c,6j,7d,7h和7j对Cdc25B抑制活性较好,抑制率分别为78.1%,71.2%,65.6%,57.2%和65.9%。2-Benzothiazolesulfenamide（ 2） was prerared by oxidation and amination from 2-mercapto benzothiazole（ 1）. 2-Benzothiazolesulfonamide（ 3） was obtained by potassium permanganate oxidation of 2. 2-Benzothiazolesulfonamide ethyl formate（ 4） was synthesized by reaction of 3 with ethyl chlorocarbonate. Ten novel 2-benzothiazolesulfonylureido amino acids（ 7a ~ 7j） were prepared by reaction of4 with L-amino acids,then hydrolyzing by Na OH. The structures were characterized by^1 H NMR,IR and ESI-MS. The inhibitory activities of 6 and 7 against Cdc25 B were investgated. The results showed that 6c,6j,7d,7h and 7j exhibited good inhibitory activities at 20 μg·m L^（-1）with inhibition rate of78. 1%,71. 2%,65. 6%,57. 2% and 65. 9%,respectively。

关 键 词：2-巯基苯并噻唑 L-氨基酸甲酯 2-苯并噻唑磺酰脲氨基酸 合成 抗肿瘤活性 

分 类 号：O626.25[理学—有机化学] O629.71[理学—化学]