Preparation of 4-azaindole and 7-azaindole dimers with a bisalkoxyalkyl spacer in order to preferentially target melatonin MT1 receptors over melatonin MT2 receptors.
Several 4-azaindole and 7-azaindole dimer analogues of melatonin with a bisalkoxyalkyl spacer between the position 5 of each heterocycle were synthetized. Our aim was to investigate the influence of the spacers length on the selectivity of such compounds for the MT(1) receptors over the MT(2) receptors. Our results suggest the distance between indole ring seems to be an important parameter in determining the potency of binding with melatonin receptor site.
Larraya
Carlos
C
EA 3247 GRCHT laboratoire de chimie organique, UFR des sciences pharmaceutiques, Université de Tours, 31, avenue de Monge, 37200 Tours, France.
Guillard
Jérôme
J
Renard
Pierre
P
Audinot
Valérie
V
Boutin
Jean A
JA
Delagrange
Philippe
P
Bennejean
Caroline
C
Viaud-Massuard
Marie-Claude
MC
D001372:Aza Compounds / Q000737:chemistry*; D001665:Binding Sites; D002453:Cell Cycle / Q000187:drug effects; D003432:Cross-Linking Reagents / Q000737:chemistry*; D019281:Dimerization; D006801:Humans; D007211:Indoles / Q000737:chemistry*; D044122:Receptor, Melatonin, MT1 / Q000378:metabolism*; D044123:Receptor, Melatonin, MT2 / Q000378:metabolism*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D001372:Aza Compounds; D003432:Cross-Linking Reagents; D007211:Indoles; D044122:Receptor, Melatonin, MT1; D044123:Receptor, Melatonin, MT2