北京林业大学学报2011，Vol.33Issue(1)：134-138,5.
3-羰基-桦木酰-甘氨酸的合成与活性分析
Synthesis and activity analysis of N-[3-oxo-20(29)-lupen-28-oyl]-glycine
摘要
Abstract
In order to enhance the biological activity of betulonic acid, 3-oxo-20 (29)-lupen-28-oic acid chloride was synthesized with betulonic acid as raw materials and oxalyl chloride as the acylating agent. Methyl ester of N-[ 3-oxo-20 ( 29 ) -lupen-28-oyl ] -glycine was synthesized by 3-oxo-20 ( 29 ) -lupen-28-oic acid chloride and methyl ester of glycine hydrochloride. N-[ 3-oxo-20 ( 29 ) -lupen-28-oyl ] -glycine was obtained by hydrolyzing methyl ester of N-[ 3-oxo-20 (29)-lupen-28-oyl ]-glycine. The structure of the product was identified by FT-IR, 1HNMR and MS spectra. Cytotoxic activity of the target product against human lung adenocarcinoma (A549) , human nose carcinoma cells (CNE) and human tongue carcinoma (Tca8113 ) cell lines was evaluated by MTr assay via the respective IC50. The result improved the structure of N-[ 3-oxo-20 ( 29 ) -lupen-28-oyl ] -glycine. HPLC results showed that the purity of synthetic product was 97. 801％. IC50 of N-[ 3-oxo-20 ( 29 ) -lupen-28-oyl ] -glycine displayed lower values than that of betulinic acid. As regards to Tca8113 cells, N-[ 3-oxo-20 ( 29 ) -lupen-28-oyl ]-glycine showed stronger activity than betulinic acid with an IC50 ratio of about 1: 11. As regards to CNE cells, N-[3oxo-20(29 )-lupen-28-oyl]-glycine showed stronger activity than betulinic acid with an IC50 ratio of about 1: 53. The bioactive assay indicates that N-[ 3-oxo-20 ( 29 ) -lupen-28-oyl] -glycine shows stronger activity than betulinic acid in resistance to tumor development.关键词
桦木酮酸/3-羰基-桦木酰-甘氨酸/肿瘤细胞/生物活性分类
化学化工引用本文复制引用
张小丽,吕坤,方桂珍,田水清,孔维..3-羰基-桦木酰-甘氨酸的合成与活性分析[J].北京林业大学学报,2011,33(1):134-138,5.基金项目
黑龙江省重大攻关项目(GB05B601). （GB05B601）
