Citation: Imerhasan, Mukhtar, Helil, Setiwaldi, Mahmud, Muhammed Amin. Synthesis and in vitro Anticancer Activity of N-Methylisoxazolinium-Salts with Carboxyl or Ester Groups against Cell Division Cycle 25B Phosphatase and Protein Tyrosine Phosphatase-1[J]. Chinese Journal of Organic Chemistry, ;2017, 37(2): 496-502. doi: 10.6023/cjoc201604033 shu

Synthesis and in vitro Anticancer Activity of N-Methylisoxazolinium-Salts with Carboxyl or Ester Groups against Cell Division Cycle 25B Phosphatase and Protein Tyrosine Phosphatase-1

  • Corresponding author: Imerhasan, Mukhtar, imerhasan@yahoo.com
  • Received Date: 15 April 2016
    Revised Date: 12 July 2016

    Fund Project: the National Natural Science Foundation of China 21462043the National Natural Science Foundation of China 21062019

Figures(1)

  • Fouteen 2-methyl-3-ethylcarboxy-5-aryl-3a, 6a-dihydro-4, 6-dioxopyrrolino[3', 4'-d]-isoxazoliniumtetrachloro-ferrate derivatives 2a~2g and 2-methyl-3-carboxyl-5-aryl-3a, 6a-dihydro-4, 6-dioxopyrrolino[3', 4'-d]-isoxazolinium-tetra-chloroferrate derivatives 4a~4g were synthesized by using dimethylsulfate as a N-methylating reagent and ferric (III)-chloride as anion exchange reagent in hydrochloric acid. The structures of the target compounds 2 and 4 were characterized by 1H NMR, IR spectra and elemental analysis. The preliminary in vitro anticancer activity on the compounds showed that most compounds possess anti-cancer activity at some extent. At the test concentration of 20 μg/mL, compounds 2a~2g and 4a~4g showed inhibition activities in the range of 97.32%~99.94% and 97.45%~99.92% against cell division cycle 25B phosphatase (Cdc25B), respectively. At the test concentration of 20 μg/mL, compounds 2a~2g and 4d~4g showed inhibition activities in the range of 52.18%~97.15% and 86.66%~99.45% against SH2-containing protein tyrosine phosphatase-1 (SHP1), respectively. Compounds 4a~4c only have the inhibition activities in the range of 15.21%~47.11%, which is lower than IC50 against SHP1. Preliminary discussion was carried out on the structure-activity relationship of the target compounds.
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    1. [1]

      Jäger, V.; Colinas, P. A. In Synthetic Applications of 1, 3-Dipolar Cycloaddtion Chemistry toward Heterocycles and Natural Products, Vol. 59, Eds.: Padwa, A.; Pearson, W. H., John Wiley & Sons, Inc., New York, 2002, pp. 361~472.

    2. [2]

      Jaeger, V.; Grund, H.; Buss, W. Bull. Soc. Chem. Belg. 1983, 92, 1039.
       

    3. [3]

      Henneböhle, M.; LeRoy, P. Y.; Jäger, V. Z. Naturforsch. 2004, 59B, 451.

    4. [4]

      Frey, W.; Imerhasan, M.; Bathich, Y.; Jäger, V. Z. Kristallogr.-New Cryst. Struct. 2005, 220, 151.
       

    5. [5]

      Bathich, Y.; Imerhasan, M.; Jäger, V. The 6th Iminiumsalz-Tagung (ImSaT-6), Stimpfach-Rechenberg, Germany, 2003, pp. 99~107.

    6. [6]

      Bathich, Y.; Henneböhle, M.; LeRoy, P. Y.; Imerhasan, M.; Jäger, V. Organische Chemie, Bad Nauheim, Germany, 2004, pp. 220~227.

    7. [7]

      Frey, W.; Henneböhle, M.; Jäger, V. Z. Kristallogr.-New Cryst. Struct. 2005, 220, 149.
       

    8. [8]

      Jäger, V.; Bathich, Y.; Shiva, S.; Li, F.; Ibrahim, M.; Henneböhle, M.; LeRoy, P. Y.; Imerhasan, M. 2nd International Conference on Heterocyclic Chemistry, University of Rajasthan, Jaipur India, 2006, pp. 1~15.

    9. [9]

      Llamas, K, ; Owens, M.; Blakeley, R. L.; Zerner, B. J. Am. Chem. Soc. 1986, 108, 5543.  doi: 10.1021/ja00278a030

    10. [10]

      Kohler, E. P.; Blatt, A. H. J. Am. Chem. Soc. 1928, 50, 1217.  doi: 10.1021/ja01391a040

    11. [11]

      Kohler, E. P.; Bruce, W. F. J. Am. Chem. Soc. 1931, 53, 644.  doi: 10.1021/ja01353a030

    12. [12]

      Bodlaender, P.; Feinstein, G.; Shaw, E. Biochemistry 1969, 8, 4941.  doi: 10.1021/bi00840a043

    13. [13]

      Ali, T.; Imerhasan, M.; Hudabergen, A. Chin. J. Org. Chem. 2012, 32, 376 (in Chinese).  doi: 10.6023/cjoc1104222
       

    14. [14]

      Li, J.-M.; Wang, J.; Liu, H.; Guo, J.-W.; Zuo, L.-F. Chin. J. Tumor 2008, 28, 586 (in Chinese).

    15. [15]

      Pagel, J. M.; Appelbaum, F. R.; Eary, J. F.; Rajendran, J.; Fisher, D. R.; Gooley, T.; Ruffner, K.; Nemecek, E.; Sickle, E.; Durack, L.; Carreras, J.; Horowitz, M. M.; Press, O. W.; Gopal, A. K.; Martin, P. J.; Bernstein, I. D.; Matthews, D. C. Blood 2006, 107, 2184.  doi: 10.1182/blood-2005-06-2317

    16. [16]

      Imerhasan, M.; Osman, K.; Muhammad, T.; Helil, S.; Haydar, G. Chin. J. Appl. Chem. 2008, 25, 931 (in Chinese).
       

    17. [17]

      Kristjansdottir, K.; Rudolph, J. Chem. Biol. 2004, 11, 1043.  doi: 10.1016/j.chembiol.2004.07.007

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