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高等学校化学研究 ›› 2016, Vol. 32 ›› Issue (3): 357-365.doi: 10.1007/s40242-016-6112-8

• Articles • 上一篇    下一篇

Synthesis and Immunosuppressive Activity of Amino Alcohol Containing Coumarin and Benzothiophene

WU Yi, SHANG Guanglei, TANG Qi, ZHANG Baozhen, WANG Ensi   

  1. College of Pharmacy, Jilin University, Changchun 130021, P. R. China
  • 收稿日期:2016-03-24 修回日期:2016-04-27 出版日期:2016-06-01 发布日期:2016-05-26
  • 通讯作者: WANG Ensi E-mail:wangss@jlu.edu.cn
  • 基金资助:

    Supported by the Fund of Jilin University(China) Hi-Tech(Group) Co. Ltd.

Synthesis and Immunosuppressive Activity of Amino Alcohol Containing Coumarin and Benzothiophene

WU Yi, SHANG Guanglei, TANG Qi, ZHANG Baozhen, WANG Ensi   

  1. College of Pharmacy, Jilin University, Changchun 130021, P. R. China
  • Received:2016-03-24 Revised:2016-04-27 Online:2016-06-01 Published:2016-05-26
  • Contact: WANG Ensi E-mail:wangss@jlu.edu.cn
  • Supported by:

    Supported by the Fund of Jilin University(China) Hi-Tech(Group) Co. Ltd.

摘要:

A series of amino alcohol derivatives containing coumarin and benzothiophene moieties was synthesized with 5-bromosalicylaldehyde and 5-bromo-2-thiophenecarboxaldehyde as starting materials, 6-substituted-3-chroma- none and 4,5-dihydrobenzo[b]-thiophen-5(4H)-one as intermediates and Suzuki reaction and spiro-hydantoin hydrolysis as key steps. The structures of key intermediate and target compounds were confirmed by 1H NMR, 13C NMR, IR and HRMS. Their characterization as sphingosine 1-phosphate(S1P) receptor agonists was reported.

关键词: Immunosuppressant, Amino alcohol derivative, Bioactivity, Suzuki reaction

Abstract:

A series of amino alcohol derivatives containing coumarin and benzothiophene moieties was synthesized with 5-bromosalicylaldehyde and 5-bromo-2-thiophenecarboxaldehyde as starting materials, 6-substituted-3-chroma- none and 4,5-dihydrobenzo[b]-thiophen-5(4H)-one as intermediates and Suzuki reaction and spiro-hydantoin hydrolysis as key steps. The structures of key intermediate and target compounds were confirmed by 1H NMR, 13C NMR, IR and HRMS. Their characterization as sphingosine 1-phosphate(S1P) receptor agonists was reported.

Key words: Immunosuppressant, Amino alcohol derivative, Bioactivity, Suzuki reaction