Substituted 3-amino and/or 3-aminomethyl-3,4-dihydro-2H-1-benzopyrans: synthesis and biological activity.
A series of new 3-amino, 3-aminomethyl-5-alkoxy-3,4-dihydro-2H-1-benzopyran and 5'-alkoxy-3',4'-dihydrospiro-[piperazine-2.3'(2'H)-benzopyran] derivatives was prepared and evaluated for affinity at 5-HT1A, 5-HT2A and D2 receptors. Two of the compounds (1f and 2b) can be considered as potent and selective 5-HT2A ligands. One compound (1g) demonstrated high affinity for 5-HT1A and D2 receptor binding sites and one compound (1d) proved to be a mixed 5-HT1A/5-HT2A ligand.
Comoy
C
C
Institut de Chimie Organique et Analytique, associé all CNRS, Université d'Orleans, France.
Guérin
V
V
Pfeiffer
B
B
Rettori
M C
MC
Renard
P
P
Guillaumet
G
G
D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D001665:Binding Sites; D006801:Humans; D020128:Inhibitory Concentration 50; D008024:Ligands; D044402:Receptor, Serotonin, 5-HT2A; D017448:Receptors, Dopamine D2 / Q000378:metabolism; D011985:Receptors, Serotonin / Q000378:metabolism; D044263:Receptors, Serotonin, 5-HT1; D013329:Structure-Activity Relationship
D000588:Amines; D001578:Benzopyrans; D008024:Ligands; D044402:Receptor, Serotonin, 5-HT2A; D017448:Receptors, Dopamine D2; D011985:Receptors, Serotonin; D044263:Receptors, Serotonin, 5-HT1; C088154:3,4-dihydro-3-amino-2H-1-benzopyran