5-substituted 3,4-dihydro-3-amino-2H-1-benzopyran derivatives: synthesis and interaction with serotoninergic receptors.
A new series of 3,4-dihydro-3-amino-2H-1-benzopyran derivatives (1 and 2) bearing various substituents on the 5-position was successfully prepared via palladium-mediated cross-coupling reactions. Some of the new compounds showed high affinity for 5-HT1A and 5-HT7 receptors. The best affinity for the 5-HT1A and 5-HT7 receptors was obtained for 2b (Ki = 0.3 nM for 5-HT1A and 3.1 nM for 5-HT7). The anxiolytic activity of compound 2b was evaluated.
Rezaie
R
R
Institut de Chimie Organique et Analytique, UMR-CNRS 6005, Université d'Orleans, France.
Joseph
B
B
Bremner
J B
JB
Delagrange
P
P
Kopp
C
C
Misslin
R
R
Pfeiffer
B
B
Renard
P
P
Guillaumet
G
G
D000818:Animals; D014151:Anti-Anxiety Agents / Q000138:chemical synthesis* / Q000378:metabolism* / Q000494:pharmacology; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000378:metabolism* / Q000494:pharmacology; D001921:Brain / Q000378:metabolism; D002417:Cattle; D003624:Darkness; D005106:Exploratory Behavior / Q000187:drug effects; D006801:Humans; D008027:Light; D051379:Mice; D011985:Receptors, Serotonin / Q000378:metabolism*; D044263:Receptors, Serotonin, 5-HT1
D014151:Anti-Anxiety Agents; D001578:Benzopyrans; D011985:Receptors, Serotonin; D044263:Receptors, Serotonin, 5-HT1; C104425:serotonin 7 receptor; C088154:3,4-dihydro-3-amino-2H-1-benzopyran