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

College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046

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.
- carboxyl,
- estergroup,
- N-methylisoxazolinium-tetrachloroferrate,
- synthesis,
- in vitro anticancer activity
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