Abstract
A still unknown tricyclic heterocyclic system (5) was synthesized from 6-hydroxy-2-methylpyridazin-3-one and its structure identified as 2,8-dichloro-6-methylpyrrolo[1,2-b:3,4-d']dipyridazin-5(6H)- one by spectroscopic investigations. Selective condensation of 5 with 2-[4-(2-substituted-phenyl)piperazin-1-yl]ethylamine gave the 2-arylpiperazinylethylamino-8-chloro derivatives 6a-c, which were investigated in binding studies toward the three alpha1-adrenergic and 5-HT1A-serotonergic receptor subtypes. They displayed high potency on all the assays and some selectivity for alpha1a and alpha1d subtypes.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Adrenergic Antagonists / chemical synthesis*
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Adrenergic Antagonists / chemistry
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Adrenergic Antagonists / pharmacology
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Animals
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Aorta, Thoracic / drug effects
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Aorta, Thoracic / physiology
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CHO Cells
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Cricetinae
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Humans
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In Vitro Techniques
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Male
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Muscle Contraction / drug effects
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Muscle, Smooth / drug effects
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Muscle, Smooth / physiology
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Pyridazines / chemical synthesis*
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Pyridazines / chemistry
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Pyridazines / pharmacology
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Pyrroles / chemical synthesis*
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Pyrroles / chemistry
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Pyrroles / pharmacology
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Radioligand Assay
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Receptors, Adrenergic, alpha-1 / biosynthesis
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Receptors, Adrenergic, alpha-1 / drug effects*
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Receptors, Serotonin / drug effects
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Receptors, Serotonin, 5-HT1
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Structure-Activity Relationship
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Vas Deferens / drug effects
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Vas Deferens / physiology
Substances
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8-chloro-2-(2-(4-(2-chlorophenyl)piperazin-1-yl)ethylamino)-6-methylpyrrolo(1,2-b 3,4-d')dipyridazin-5(6H)-one
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8-chloro-2-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethylamino)-6-methylpyrrolo(1,2-b 3,4-d')dipyridazin-5(6H)-one
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8-chloro-2-(2-(4-phenylpiperazin-1-yl)ethylamino)-6-methylpyrrolo(1,2-b 3,4-d')dipyridazin-5(6H)-one
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Adrenergic Antagonists
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Pyridazines
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Pyrroles
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Receptors, Adrenergic, alpha-1
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Receptors, Serotonin
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Receptors, Serotonin, 5-HT1