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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (08): 1001-1006. 上一篇    下一篇

研究简报

α-取代氨基氟代苯基膦酸酯衍生物的合成、晶体结构与抗癌活性

宋宝安*，洪艳平，金林红，杨松，邹志辉，
胡德禹，何伟，刘刚，张国平，李黔柱   

  1. (1教育部绿色农药与农业生物工程重点实验室 贵阳 550025)
  • 收稿日期:2004-07-14 修回日期:2005-02-25 发布日期:2005-07-30
  • 通讯作者: 宋宝安

Synthesis, Structure and Antitumor Activity of α-Substituted Aminofluoroarylphosphonate Derivitaves

SONG Bao-An*,HONG Yan-Ping,JIN Lin-Hong,YANG Song,ZOU Zhi-Hui
HU De-Yu,HE Wei,LIU Gang,ZHANG Guo-Ping,LI Qian-Zhu   

  1. (1 Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guiyang 550025)
    (2 Center for Reserch and Development of Fine Chemicals, Guizhou University, Guiyang 550025)
  • Received:2004-07-14 Revised:2005-02-25 Published:2005-07-30
  • Contact: SONG Bao-An

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利用席夫碱与亚磷酸酯反应, 合成了新型O,O'-二烷基-α-(6-甲氧苯并噻唑-2-基氨基)-4-氟苯基膦酸酯化合物, 结构经元素分析, IR, 1H NMR, 13C NMR和X单晶衍射确认. X单晶衍射测试结果表明: 化合物3d分子属于四面体晶系, 空间群I4(1)/a, a＝2.1055(3) nm, b＝2.1055(3) nm, c＝2.0521(5) nm, α＝90.00°, β＝90.00°, γ＝90.00°, V＝0.9098(3) nm3, Z＝16, Dc＝1.321 mg/m3, ＝0.250 mm－1, F(000)＝3808. 化合物还存在着1个分子内氢键[N(2)—H(2)…O(1)]. 生物测定表明化合物3f在20 g/mL浓度下对PC3细胞的抑制率为84.3%.

关键词: α-氨基膦酸酯, 苯并噻唑, 抗癌活性, 合成

Some novel O,O'-diakyl-α-(6-methoxybenzothiazol-2-ylamino)-4-fluorophenylphosphonates (3) have been synthesized through the reaction of Schiff base with dialkyl phosphite. Their struc-tures were clearly established by elemental analysis, IR, 1H NMR, 13C NMR and X-ray diffraction analysis. The crystal of compound 3d belongs to tetragonal with space group I4(1)/a, a＝2.1055(3) nm, b＝2.1055(3) nm, c＝2.0521(5) nm, α＝90.00°, β＝90.00°, γ＝90.00°, V＝0.9098(3) nm3, Z＝16, Dc＝1.321 mg/m3, α＝0.250 mm－1, F(000)＝3808. There exists an intramolecular hydrogen bond [N(2)—H(2)…O(1)] in the molecule of 3d. Bioassay tests showed that compound 3f could inhibit PC3 cell proliferation at the concentration of 20 g/mL with the inhibition rate 84.3%.

Key words: α-aminophosphonate, synthesis, antitumor activity, benzothiazole