摘要
微波辅助下,采用水杨酸与α-羟基膦酸酯在DCC/DMAP催化下酯化,合成了12个结构新颖的水杨酰氧基膦酸酯衍生物,其结构经IR,1H NMR,13C NMR及元素分析确认.优化得最适微波合成条件:以15 m L CH2Cl2为溶剂,辐射功率800 W,室温反应3.5 h,有最好产率,该方法具有反应时间较短、产率较高等优点.四甲基偶氮唑蓝(MTT)法测试了目标化合物的抗肿瘤活性,结果表明:目标化合物对所测试的四种肿瘤细胞均有增殖抑制作用.其中化合物2f对HEp-2的抑制活性[IC50=(13.9±0.6)μmol/L]略低于对照药[IC50=(9.3±1.1)μmol/L],化合物2k对EC-109的抑制活性[IC50=(8.5±0.9)μmol/L]接近对照药[IC50=(5.9±1.0)μmol/L].
Twelve new salicyl acyloxy phosphonate derivatives were synthesized via microwave-assisted reactions of sali-cylic acid withα-hydroxyphosphonate in DCC/DMAP. The structures of the products were confirmed by elemental analysis, IR, 1H NMR and 13C NMR data. The suitable synthetic conditions were as follows：in 15 mL of CH2Cl2 with power 800 W at room temperature for 3.5 h. The cytotoxic activities of all compounds on A-549, SGC-7901, HEp-2 and EC-109 in vitro were evaluated by using an 3-（4,5-dimethylthiazol-2-yl）-2,5-diphenyl tetrazolium bromide （MTT） method, and some of them showed good antitumor activity. Among the active compounds, espectively, compound 2f had better inhibition effect on HEp-2 cells growth [IC50=（13.9±0.6）μmol/L], the IC50 values of compound 2k was （8.5±0.9）μmol/L against EC-109 cells, similar to cisplatin [IC50=（5.9±1.0）μmol/L].
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2014年第12期2566-2571,共6页
Chinese Journal of Organic Chemistry
基金
贵州省科技厅基金(No.黔科合外G字[2014]7013)
贵州省教育厅(No.黔科合人才团队字[2012]03号)资助项目~~
关键词
水杨酸
α-羟基膦酸酯
微波辐射
合成
抗肿瘤活性
salicylic acid
α-hydroxyphosphonate
microwave irradiation
synthesis
antitumor activity
