Design, synthesis, and melatoninergic activity of new azido- and isothiocyanato-substituted indoles.
To develop irreversibly binding ligands for the melatonin receptor(s) as tools for tracing the primary melatonin binding site, we report on the design and synthesis of new melatoninergic azido- and isothiocyanato-substituted indoles. All active compounds were partial agonists or antagonists in the Xenopus melanophore assay, the most potent being the 5-OMe C3-substituted azido 45 and isothiocyanato 46 analogues.
Tsotinis
Andrew
A
Faculty of Pharmacy, Department of Pharmaceutical Chemistry, University of Athens, Panepistimioupoli-Zografou, 157 71 Athens, Greece. tsotinis@pharm.uoa.gr
Afroudakis
Pandelis A
PA
Davidson
Kathryn
K
Prashar
Anjali
A
Sugden
David
D
D000818:Animals; D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017879:Isothiocyanates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008024:Ligands; D008550:Melatonin / Q000378:metabolism*; D044094:Receptors, Melatonin / Q000819:agonists* / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship; D014982:Xenopus laevis
D001386:Azides; D007211:Indoles; D017879:Isothiocyanates; D008024:Ligands; D044094:Receptors, Melatonin; D008550:Melatonin