Synthesis of new tricyclic melatoninergic ligands.
We report the synthesis and biological evaluation of a series of new tricyclic analogs of the hormone melatonin, which act as probes of the constraints at the hormone's receptor site with regard to the lower N1-C2 region of the indole moiety of melatonin. Three of the new compounds, N-[2-(2-methoxy-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)ethyl]acetamide (9), and the respective propionamide 10 and butyramide 11, are as potent as melatonin in the Xenopus laevis melanophore model.
Tsotinis
A
A
School of Pharmacy, Department of Pharmaceutical Chemistry, University of Athens, Greece. tsotinis@pharm.uoa.gr
Panoussopoulou
M
M
Sivananthan
S
S
Sugden
D
D
D000818:Animals; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D008024:Ligands; D008547:Melanophores / Q000187:drug effects; D008550:Melatonin / Q000819:agonists / Q000031:analogs & derivatives* / Q000037:antagonists & inhibitors; D014982:Xenopus laevis
D007211:Indoles; D008024:Ligands; D008550:Melatonin