Abstract
A small set of 2-{4-[3-(4-aryl/heteroaryl-piperazinyl)propoxy]phenyl}-2H-benzo tri azoles and corresponding N-oxides were prepared. The synthesized compounds were able to bind on some serotonin (5-HT1A, 5-HT2A) and dopamine (D2, D3) receptors, while displaying poor or no affinity for 5-HT1B, 5-HT2C, 5-HT3, and 5-HT4 subtypes. The strong contribution of the N-oxide function for the binding on 5-HT1A, D2 and D3 receptors is noteworthy. For 2-{4-[3-[4-(2-methoxyphenyl)-1-piperazinyl]propoxy]phenyl}-2H-benzotr iazole- 1-oxide (4b), the binding constants (Ki) were 11.9 (5-HT1A) and 10.5 nM (D3). In a general pharmacological screening, the 2-{4-[3-(4-phenyl-1-piperazinyl)propoxy]phenyl}-2H-benzotriazole (3a) exhibited only very weak activities, with the exception of protecting mice from cyanide-induced hypoxia.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Binding, Competitive / drug effects
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Dopamine Agents / chemical synthesis*
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Dopamine Agents / pharmacology
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Dopamine Agonists / metabolism
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Ligands
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Magnetic Resonance Spectroscopy
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Mice
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Neostriatum / drug effects
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Neostriatum / metabolism
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Olfactory Bulb / drug effects
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Olfactory Bulb / metabolism
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Radioligand Assay
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Rats
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Receptors, Dopamine / drug effects
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Receptors, Serotonin / drug effects
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Serotonin Agents / chemical synthesis*
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Serotonin Agents / pharmacology
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Spectrophotometry, Ultraviolet
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Spiperone / metabolism
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Structure-Activity Relationship
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Tetrahydronaphthalenes / metabolism
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Triazoles / chemical synthesis*
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Triazoles / pharmacology
Substances
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Dopamine Agents
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Dopamine Agonists
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Ligands
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Receptors, Dopamine
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Receptors, Serotonin
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Serotonin Agents
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Tetrahydronaphthalenes
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Triazoles
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Spiperone
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7-hydroxy-2-N,N-dipropylaminotetralin