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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (12): 1884-1889. 上一篇    下一篇

研究论文

含吖啶基的新型二氧代氮杂茂并[3,4-d]异噁唑衍生物的合成及其生物活性研究

穆赫塔尔•伊米尔艾山*,1，王婷1，萨提瓦力迪•海力力1，库尔班•吾斯曼2，吐尔洪•买买提1   

  1. (1新疆大学化学与化工学院 乌鲁木齐 830046)
    (2喀什师范学院生命与环境科学系 喀什 844007)
  • 收稿日期:2010-01-07 修回日期:2010-07-09 发布日期:2010-07-23
  • 通讯作者: 穆赫塔尔·伊米尔艾山 E-mail:imerhasan@xju.edu.cn

Synthesis and Bioactivity of Novel Pyrrolino[3 ,4 -d]isoxazole Derivatives Containing Acridinyl

Imerhasan Mukhtar*,1 Wang Ting1 Helil Seti-waldi1 Osman Kurban2 Muhammad Turghun1   

  1. (1 College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046)
    (2 Department of Life and Environmental Science, Kashgar Teacher s Col-lege, Kashgar 844007)
  • Received:2010-01-07 Revised:2010-07-09 Published:2010-07-23
  • Contact: Imerhasan Mukhtar E-mail:imerhasan@xju.edu.cn

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在三乙胺的作用下, N-芳基-马来酰亚胺分别与α-氯代9-吖啶甲醛肟和N-(N,N-对二甲氨基苯基)-C-(9-吖啶基)取代硝酮发生1,3-偶极环加成反应, 合成了13个未见文献报道的新型3-(9-吖啶基)-5-芳基-3a,6a-二氢-4,6-二氧代氮杂茂并[3 ,4 -d]异噁唑啉衍生物3a～3f和2-(N,N-对二甲氨基苯基)-3-(9-吖啶基)-5-芳基-3a,6a-二氢-4,6-二氧代氮杂茂并[3 ,4 -d]异噁唑烷衍生物4a～4g, 其结构经1H NMR, IR和元素分析确证. 并对化合物3和4进行了初步药物活性筛选, 其对HL-60人白血病细胞生长具有不同程度的抑制作用, 但当样品浓度为10 μmol/L时, 抑制率为0～35% (IC50＜50%). 化合物3f和4g对细胞分裂周期磷酸酯酶Cdc25A具有抑制作用：当样品浓度为20 μg/mL时, 其抑制率分别为50.90%和51.22%.

关键词: 吖啶基, 二氧代氮杂茂并[3, 4 -d]异噁唑, 合成, 生物活性

Thirteen novel pyrrolino[3 ,4 -d]isoxazol derivatives were synthesized through 1,3-dipolar cycloaddition reaction of N-arylmaleimide with α-chloro-9-acridinylformoxime or N-(N,N-dimethylanilin)-C-(9-acridinyl)nitrone in the presence of triethyl-amine. These compounds include 3-(9-acridin- yl)-5-aryl-3a,6a-dihydro-4,6-dioxopyrrolino[3 ,4 -d]isoxazoline derivatives 3a～3f and 2-(N,N-dimethyl- ani-lin)-3-(9-acridinyl)-5-aryl-3a,6a-dihydro-4,6-dioxopyrrolino[3 ,4 -d]isoxazolidine de-rivatives 4a～4g. All the compounds were identified by 1H NMR, IR spectra and elemental analysis. The bioactivities of compounds 3 and 4 were evaluated by pre-liminary bioassay and they exhibited different extent of Leucocythemia activities against Human HL-60. At the test concentration of 10 μmol/L, the inhibition activities were in the range of 0～35%, which is lower than IC50. Compounds 3f and 4g showed Cdc25A (Cell division cycle 25A) inhibition activity of 50.90% and 51.22% respectively at the test concentration of 20 μg/mL.

Key words: acridinyl, dioxo-pyrrolino[3, 4 -d]isoxazole, synthesis, bioactivity