氨基糖衍生物二丁基锡配合物的合成、结构表征和生物活性  

Synthesis,Characterization and in vitro Antitumor Activity of Dibutyltin Complexes of Aminoglucosyl Derivatives

作　　者：张艳霞[1] 薛学温[2] 万升标[1] 江涛[1] 

机构地区：[1]中国海洋大学食品与药物研究所,青岛266003 [2]青岛医学院附属医院,青岛266021

出　　处：《有机化学》2007年第1期97-102,共6页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.20371043);中法先进研究计划(No.PRAB03-04)资助项目.

摘　　要：分别由2-[(2Z)-3-羧基-1-氧代-2-丙烯基]氨基-2-脱氧-1,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖(1a),2-[(2-羧基苯甲酰基)氨基]-2-脱氧-1,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖(2a)和氧化二正丁基锡反应合成了两个新化合物双-{2-[(2Z)-3-羧基-1-氧代-2-丙烯基]氨基-2-脱氧-1,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖}-二正丁基锡酯(1)和双-{2-[(2-羧基苯甲酰基)氨基]-2-脱氧-1,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖}-二正丁基锡酯(2),并经红外光谱、核磁共振(1H,13CNMR)、质谱初步确定了其结构.体外抗肿瘤活性结果表明,化合物1对人肺癌细胞株A-549和人肝癌细胞株BEL-7402的细胞毒活性显示为强效;而对小鼠白血病细胞株P388和人白血病细胞株HL-60的细胞毒活性为弱效.化合物2对肿瘤细胞株HL-60,A-549和BEL-7402具有强效的细胞毒活性;而对肿瘤细胞株P388的作用则为弱效.克隆基因分析表明化合物1和2在3.82×10-6和3.02×10-6mol/L均具有造血细胞毒性.Di（n-butyl）tin（IV） oxide reacts with the amino glucose analogues, 1,3,4,6-tetra-O-acetyl-2- {[（2Z）-3-carboxy-l-oxo-2-propenyl]amino}-2-deoxy-β-D-glucopyranose （la） and 1,3,4,6-tetra-O-acetyl-2- [（2-carboxybenzoyl）amino]-2-deoxy-β-D-glucopyranose （2a） to give the complexes bis-[1,3,4,6-tetra-O- acetyl-2-{[（2Z）-3-carboxy-1-oxo-2-propenyl]amino}-2-deoxy-β-D-glucopyranose]-di-n-butyltin carboxylate （1） and bis-{ 1,3,4,6-tetra-O-acetyl-2-[（2-carboxybenzoyl）amino]-2-deoxy-β-D-glucopyranose}-di-n-butyltin carboxylate （2） which have been characterized by IR and ^1H, ^13C NMR and MS spectra. The results of in vitro tests show that compound 1 exhibits high cytotoxicity against the tumor cell lines of A-549 and BEL-7402, low cytotoxicity against the tumor cell lines of P388 and HL-60, while compound 2 exhibits high cytotoxicity against the tumor cell lines of HL-60, A-549 and BEL-7402, low cytotoxicity against the tumor cell line of P388. Clone gene analysis shows that compounds 1 and 2 both have hematopoietic cell toxicity at the concentration of 3.82 ×10^6 and 3.02 ×10^6 mol/L, respectively .

关 键 词：有机锡羧酸酯 合成 结构表征 抗肿瘤活性 造血细胞毒性 

分 类 号：O641.4[理学—物理化学]