Design, synthesis, and discovery of 5-piperazinyl-1,2,6,7-tetrahydro-5H-azepino[3,2,1-hi]indol-4-one derivatives: A novel series of mixed dopamine D2/D4 receptor antagonist

Three styryl-substituted tetrahydro-1,4-epoxy-1-benzazepines: configurations, conformations and hydrogen-bonded chains

“…The tetrahydro-1-benzazepine system is an important pharmacophore in drug discovery and many of its derivatives exhibit a broad spectrum of biological activity (Zuccotto et al, 2001;Fabio et al, 2003;Zhao et al, 2003;Seto et al, 2005;Shimada et al, 2005;Kunick et al, 2006). Accordingly, a number of synthetic methods have recently been developed for the synthesis of new derivatives of this heterocyclic system (Fujita et al, 2004;Ikemoto et al, 2005;Qadir et al, 2005).…”

Update 1 of: Recent Progress in Development of Dopamine Receptor Subtype-Selective Agents: Potential Therapeutics for Neurological and Psychiatric Disorders

“…402 Among tricyclic and bicyclic analogs designed to further rigidify the carboxamido moiety, compounds 484 and 485 were potent at D 4 receptors (K i = 5 and 4 nM) and showed 29-and 42-fold of D 4 /D 2 selectivity. 403 Similar D 4 affinity and D 4 /D 2 selectivity were found on the conformationally constrained bicyclic acetamides 486 and 487. 404 These mixed D 4 /D 2 profiles are similar to that of clozapine but the α 1 affinity was not observed.…”

(2R*,4S*)-2-(Pyridin-3-yl)-2,3,4,5-tetrahydro-1H-1-benzazepin-4-ol: a three-dimensional framework built from O—H...N, C—H...O and C—H...π(arene) hydrogen bonds

“…The chemistry of tetrahydro-1-benzazepine systems has been extensively investigated, and many examples of this class have been the targets in synthetic investigations because of their known biological properties, such as nonpeptide arginine vasopressin antagonists for both V1A and V2 receptors (Tsunoda et al, 2005), inhibitors of cyclin-dependent kinases (Kunick et al, 2006), agents against HIV-1 infection (Seto et al, 2005) and antipsychotic agents (Zhao et al, 2003). The growing interest in tetrahydro-1-benzazepines has recently been boosted by their high potential value as agents against promastigotes and amastigotes of Leishmania mexicana (Knockaert et al, 2002), and as inhibitors of Trypanosoma cruzi dihydrofolate reductase (Zuccotto et al, 2001).…”