Design and synthesis of new N-OMe fluoro-indole melatoninergics.
The synthesis of a series of new N-OMe fluoro-indoles with melatoninergic activity in the Xenopus melanophore assay is described. All of the 4-F substituted compounds, 22a-e and 25a,b, were antagonists on the clonal Xenopus melanophore line. Conversely, the 5-F substituted analogs (15a-e) did not share the same pharmacological profile, as two of them, compounds 15d (R=c-C(3)H(5)) and 15e (R=c-C(4)H(7)), exhibited a weak agonistic and partial agonistic activity, respectively, whilst the other three (15a-c) were all agonists. It seems that in this case the nature of the response (agonist or antagonist activity) is solely dependent on the shape of the R group.
Faculty of Pharmacy, Department of Pharmaceutical Chemistry, University of Athens, Panepistimioupoli-Zografou, 15771 Athens, Greece. tsotinis@pharm.uoa.gr
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A
Tsotinis
J
J
Gourgourinis
A
A
Eleutheriades
K
K
Davidson
D
D
Sugden
D000818:Animals; D015195:Drug Design; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D008547:Melanophores / Q000187:drug effects*; D008550:Melatonin / Q000819:agonists* / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship; D014981:Xenopus
D007211:Indoles; C030374:indole; D008550:Melatonin