Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (02): 376-381 .DOI: 10.6023/cjoc1104222 Previous Articles     Next Articles

Articles

新型二氧代氮杂茂并[3',4'-d]N-甲基异噁唑四氯化铁酸盐衍生物的合成及其生物活性

图尔麦麦提·艾力, 穆赫塔尔·伊米尔艾山, 阿依努尔·胡达依别尔根   

  1. 新疆大学化学与化工学院 乌鲁木齐 830046
  • 收稿日期:2011-04-22 修回日期:2011-09-14 发布日期:2012-03-09
  • 通讯作者: 穆赫塔尔·伊米尔艾山 E-mail:imerhasan@xju.edu.cn
  • 基金资助:

    国家自然科学基金(No. 21062019)资助项目.

Synthesis and Bioactivity of Novel Dioxy-pyrrolino[3',4'-d]-N-methylisoxazolinium-tetrachloroferrate Derivatives

Turmuhammad Ali, Mukhtar Imerhasan, Aynur Hudabergen   

  1. College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046
  • Received:2011-04-22 Revised:2011-09-14 Published:2012-03-09
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21062019).

Fifteen novel 2-methyl-3-(1',2'-O-cyclohexylidendioxyethyl)-5-aryl-3a,6a-dihydro-4,6-dioxopyrrolino[3',4'-d]- isoxazolinium-tetrachloroferrate derivatives 4a4o were synthesized by N-methylation of the corresponding isoxazoline using dimethyl sulfate as a methylating reagent and ferric(III)-chloride as anion exchange reagent in hydrochloric acid. The structures of the target compounds 4a4o were characterized by 1H NMR, IR spectra and elemental analysis. The preliminary in vitro bioassay on the compounds showed that most compounds possess anti-cancer activity and the Leukocyte common antigen activity at some extent. At the test concentration of 20 μg/mL, all compounds showed inhibition activity of ≥97.55% against Cdc25B (cell division cycle 25B) phosphatase except for compound 4h, and inhibition activity of 68.41%~93.38% against leukocyte common antigen (LCK) CD45 protein tyrosine phosphatase A, respectively. Preliminary discussion was carried out on the structure-activity relationship of the target compounds.

Key words: N-methylisoxazolinium-tetrachloroferrate, synthesis, bioactivity