Herein we report attempts to optimize the pharmacological properties of 5-(2-hydroxyethoxy)-N-acetyltryptamine (5-HEAT), a melatonin receptor ligand previously described by us. Several 5-substituted and 2,5-disubstituted N-acyltryptamines were synthesized and evaluated in vitro for the human cloned MT1 and MT2 receptors. Fromthis series of N-acyltryptamines the 2-bromo derivative (5c) retains the interesting efficacy profile of 5-HEAT and shows increased melatonin receptor affinities; it represents one of the first examples of a high-affinity MT1 agonist/MT2 antagonist. Some other full agonists for both melatonin receptors which exhibit similar or increased affinity relative to that of melatonin were obtained.
Towards the development of mixed MT(1)-agonist/MT(2)-antagonist melatonin receptor ligands / G. Spadoni, A. Bedini, T. Guidi, G. Tarzia, V. Lucini, M. Pannacci, F. Fraschini. - In: CHEMMEDCHEM. - ISSN 1860-7179. - 1:10(2006 Oct), pp. 1099-1105.
Towards the development of mixed MT(1)-agonist/MT(2)-antagonist melatonin receptor ligands
V. Lucini;M. PannacciPenultimo
;F. FraschiniUltimo
2006
Abstract
Herein we report attempts to optimize the pharmacological properties of 5-(2-hydroxyethoxy)-N-acetyltryptamine (5-HEAT), a melatonin receptor ligand previously described by us. Several 5-substituted and 2,5-disubstituted N-acyltryptamines were synthesized and evaluated in vitro for the human cloned MT1 and MT2 receptors. Fromthis series of N-acyltryptamines the 2-bromo derivative (5c) retains the interesting efficacy profile of 5-HEAT and shows increased melatonin receptor affinities; it represents one of the first examples of a high-affinity MT1 agonist/MT2 antagonist. Some other full agonists for both melatonin receptors which exhibit similar or increased affinity relative to that of melatonin were obtained.Pubblicazioni consigliate
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