Chemical Research in Chinese Universities ›› 2016, Vol. 32 ›› Issue (3): 357-365.doi: 10.1007/s40242-016-6112-8

• Articles • Previous Articles     Next Articles

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.

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