Design and synthesis of benzofuranic derivatives as new ligands at the melatonin-binding site MT3.
Benzofuranic analogues of MCA-NAT (5-methoxycarbonylamino-N-acetyltryptamine) have been synthesized and evaluated as melatonin receptor ligands. Introduction of a methoxycarbonylamino substituent in the C-5 position of the benzofurane nucleus obtains MT(3) selective ligands. This selectivity can be modulated with suitable variations of the C-5 position and the acyl group on the C-3 side chain.
Ettaoussi
Mohamed
M
Laboratoire de Chimie Thérapeutique (EA 1043), Faculté des Sciences Pharmaceutiques et Biologiques, Université de Lille, 3, rue du professeur Laguesse, 2, BP 83, 59006 Lille Cedex, France.
Péres
Basile
B
Klupsch
Fréderique
F
Delagrange
Philippe
P
Boutin
Jean-A
JA
Renard
Pierre
P
Caignard
Daniel-H
DH
Chavatte
Philippe
P
Berthelot
Pascal
P
Lesieur
Daniel
D
Yous
Saïd
S
D001665:Binding Sites; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D020128:Inhibitory Concentration 50; D008024:Ligands; D008550:Melatonin / Q000737:chemistry*; D015394:Molecular Structure; D044094:Receptors, Melatonin / Q000187:drug effects*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014363:Tryptamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
C413586:5-methoxycarbonylamino-N-acetyltryptamine; D008024:Ligands; D044094:Receptors, Melatonin; D014363:Tryptamines; D008550:Melatonin