22359-26-8Relevant academic research and scientific papers
Dopamine Receptor Ligands. Part VII [1]: Novel 3-Substituted 5-Phenyl-1,2,3,4,5,6-hexahydro-azepino-[4,5-b]indoles as Ligands for the Dopamine Receptors
Decker, Michael,Lehmann, Jochen
, p. 466 - 476 (2007/10/03)
A number of 5-phenyl-1,2,3,4,5,6-hexahydro-azepino-[4,5-b]indoles 3 were synthesized with different substituents at the azepine-N position (methyl-, allyl-, 2-phenyl-ethyl-, cyclopropylmethyl- and unsubstituted). Furthermore, the indole-N-methylated compound was generated and by using norephedrines and norpseudoephedrines as a chiral pool, 4-methyl-5-phenyl-1,2,3,4,5,6-hexahydro-azepino-[4,5-b]indoles were prepared which contained racemisation at the reacting C-atom. These compounds, as well as the ring-open amino-alcohols, were screened for their affinity to the hD 1-, hD5-, hD2L-, and hD4-receptors (s please check sentence). They had micromolar affinities for the receptors and showed the highest affinity to the D1-subtype family. The cyclic compounds possessed the highest affinity, with the cyclo-propylmethyl-(3 c) and methyl-substituents (3 e) being the most active of the tested compounds. Based on an intracellular cAMP-assay, the unsubstituted compound (at the azepine-N position) turned out to be an agonist for the D 1- and D5-subtype family, whereas the substituted compounds showed (partial) agonistic, or even inverse agonistic activity.
