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

doi:10.6023/cjoc201604033

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (2): 496-502.DOI: 10.6023/cjoc201604033 Previous Articles Next Articles

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含羧基或酯基的N-甲基异噁唑啉盐的合成及其对细胞分裂周期25B磷酸酯酶和蛋白酪氨酸磷酸酶1的体外抗癌活性

穆赫塔尔·伊米尔艾山, 萨提瓦力迪·海力力, 麦麦提依明·马合木提

新疆大学化学与化工学院乌鲁木齐 830046

收稿日期:2016-04-15 修回日期:2016-07-12 发布日期:2016-09-06
通讯作者: 穆赫塔尔·伊米尔艾山 E-mail:imerhasan@yahoo.com
基金资助:
国家自然科学基金（Nos.21462043，21062019）资助项目.

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

Imerhasan Mukhtar, Helil Setiwaldi, Mahmud Muhammed Amin

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

Received:2016-04-15 Revised:2016-07-12 Published:2016-09-06
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21462043, 21062019).

1. 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.PDF(12382KB)

Abstract

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.

Key words: carboxyl, estergroup, N-methylisoxazolinium-tetrachloroferrate, synthesis, in vitro anticancer activity

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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]. Chin. J. Org. Chem., 2017, 37(2): 496-502.

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含羧基或酯基的N-甲基异噁唑啉盐的合成及其对细胞分裂周期25B磷酸酯酶和蛋白酪氨酸磷酸酶1的体外抗癌活性

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

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