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有机化学 ›› 2007, Vol. 27 ›› Issue (01): 97-102. 上一篇    下一篇

研究论文

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

张艳霞a，薛学温b，万升标a，江涛*,a   

  1. (a中国海洋大学食品与药物研究所 青岛 266003)
    (b青岛医学院附属医院 青岛 266021)
  • 收稿日期:2006-04-03 修回日期:2006-05-12 发布日期:2006-12-30
  • 通讯作者: 江涛

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

ZHANG Yan-Xiaa,XUE Xue-Wenb,WAN Sheng-Biaoa,JIANG Tao*,a   

  1. (a Marine Food and Drug Institute, Ocean University of China, Qingdao 266003)
    (b The Affiliated Hospital of Qingdao Medical College, Qingdao 266021)
  • Received:2006-04-03 Revised:2006-05-12 Published:2006-12-30
  • Contact: JIANG Tao

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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, 13C NMR)、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 3.02×10－6 mol/L均具有造血细胞毒性.

关键词: 结构表征, 抗肿瘤活性, 造血细胞毒性, 有机锡羧酸酯, 合成

Di(n-butyl)tin(IV) oxide reacts with the amino glucose analogues, 1,3,4,6-tetra-O-acetyl-2- {[(2Z)-3-carboxy-1-oxo-2-propenyl]amino}-2-deoxy-β-D-glucopyranose (1a) 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

Key words: structural characterization, antitumor activity, synthesis, hematopoietic cell toxicity, organotin carboxylate