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Title

Novel N-acetyl bioisosteres of melatonin: Melatonergic receptor pharmacology, physicochemical studies, and phenotypic assessment of their neurogenic potential

AuthorsFuente Revenga, Mario de la; Fernández-Sáez, Nerea ; Herrera-Arozamena, Clara; Morales-García, José A. ; Alonso-Gil, Sandra ; Pérez Castillo, Ana ; Caignard, Daniel-Henri; Rivara, Silvia; Rodríguez-Franco, María Isabel
Issue Date2015
PublisherAmerican Chemical Society
CitationJournal of Medicinal Chemistry 58(12): 4998-5014 (2015)
AbstractHerein we present a new family of melatonin-based compounds, in which the acetamido group of melatonin has been bioisosterically replaced by a series of reversed amides and azoles, such as oxazole, 1,2,4-oxadiazole, and 1,3,4-oxadiazole, as well as other related five-membered heterocycles, namely, 1,3,4-oxadiazol(thio)ones, 1,3,4-triazol(thio)ones, and an 1,3,4-thiadiazole. New compounds were fully characterized at melatonin receptors (MT<inf>1</inf>R and MT<inf>2</inf>R), and results were rationalized by superimposition studies of their structures to the bioactive conformation of melatonin. We also found that several of these melatonin-based compounds promoted differentiation of rat neural stem cells to a neuronal phenotype in vitro, in some cases to a higher extent than melatonin. This unique profile constitutes the starting point for further pharmacological studies to assess the mechanistic pathways and the relevance of neurogenesis induced by melatonin-related structures.
Descriptionet al.
URIhttp://hdl.handle.net/10261/123461
DOI10.1021/acs.jmedchem.5b00245
Identifiersdoi: 10.1021/acs.jmedchem.5b00245
issn: 0022-2623
e-issn: 1520-4804
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