Chin. J. Org. Chem. ›› 2007, Vol. 27 ›› Issue (01): 97-102. Previous Articles     Next Articles

Original Articles

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

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