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(4 H )-one as intermediates and Suzuki reaction...

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Bibliographic Details
Published inChemical research in Chinese universities Vol. 32; no. 3; pp. 357 - 365
Main Authors Wu, Yi, Shang, Guanglei, Tang, Qi, Zhang, Baozhen, Wang, Ensi
Format Journal Article
LanguageEnglish
Published Changchun Jilin University and The Editorial Department of Chemical Research in Chinese Universities 01.06.2016
Subjects
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Physical Chemistry
Immunosuppressant
Amino alcohol derivative
Bioactivity
Suzuki reaction
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Summary: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(4 H )-one as intermediates and Suzuki reaction and spiro-hydantoin hydrolysis as key steps. The structures of key intermediate and target compounds were confirmed by 1 H NMR, 13 C NMR, IR and HRMS. Their characterization as sphingosine 1-phosphate(S1P) receptor agonists was reported.
ISSN:1005-9040
2210-3171
DOI:10.1007/s40242-016-6112-8