Synthesis and immunosuppressive activity of amino alcohol containing coumarin and benzothiophene

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-chromanone 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.