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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 02: 376 - 381

DOI: https://doi.org/10.6023/cjoc1104222

Articles

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

  • Turmuhammad Ali ,
  • Mukhtar Imerhasan ,
  • Aynur Hudabergen
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  • College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046

Received date: 2011-04-22

  Revised date: 2011-09-14

  Online published: 2012-03-09

Supported by

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

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Abstract

Fifteen novel 2-methyl-3-(1',2'-O-cyclohexylidendioxyethyl)-5-aryl-3a,6a-dihydro-4,6-dioxopyrrolino[3',4'-d]- isoxazolinium-tetrachloroferrate derivatives 4a～4o 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 4a～4o 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

Cite this article

Turmuhammad Ali , Mukhtar Imerhasan , Aynur Hudabergen . Synthesis and Bioactivity of Novel Dioxy-pyrrolino[3',4'-d]-N-methylisoxazolinium-tetrachloroferrate Derivatives[J]. Chinese Journal of Organic Chemistry, 2012 , 32(02) : 376 -381 . DOI: 10.6023/cjoc1104222

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