Synthesis of 5-substituted-2,3-dihydro-1,4-benzoxathiins: biological evaluation as melatonin receptors ligands.
The synthesis of benzoxathiins bearing a retroamide function is described from 8-hydroxythiochroman, the key step involving the synthesis of the benzoxathiin ring through a sulfonium salt. These new melatonin analogues were evaluated on human receptors MT1 and MT2 and have a similar affinity to that of melatonin itself.
Charton
Isabelle
I
Institut de Chimie Organique et Analytique, UMR-CNRS 6005, Université d'Orléans, rue de Chartres, BP 6759, 45067 Orléans Cedex 02, France.
Suzenet
Franck
F
Boutin
Jean A
JA
Audinot
Valérie
V
Delagrange
Philippe
P
Bennejean
Caroline
C
Renard
Pierre
P
Guillaumet
Gérald
G
D000818:Animals; D001667:Binding, Competitive; D002460:Cell Line; D006801:Humans; D008024:Ligands; D008550:Melatonin / Q000031:analogs & derivatives* / Q000378:metabolism; D015394:Molecular Structure; D010075:Oxathiins / Q000138:chemical synthesis* / Q000494:pharmacology*; D044122:Receptor, Melatonin, MT1 / Q000378:metabolism*; D044123:Receptor, Melatonin, MT2 / Q000378:metabolism*; D013329:Structure-Activity Relationship
D008024:Ligands; D010075:Oxathiins; D044122:Receptor, Melatonin, MT1; D044123:Receptor, Melatonin, MT2; D008550:Melatonin