Abstract
(R)-1,2,3,4-Tetrahydro[1]benzothieno[2,3-c]pyridine derivatives (60-114) were synthesized. The (R)-isomers have affinity for the 5-HT1A receptor while the (S)-isomers have no such ability. The affinity of the (R)-isomers was discussed on the basis of structure-activity relationships between the affinity and hydrophobicity of the (R)-isomers. Compounds 71 and 107, which are representative derivative compounds, have anticonflict activity and lessening of memory impairment. In particular, compound 107 cannot bind to receptors other than the 5-HT1A receptor, demonstrating that it is a unique compound with a different mechanism of action from that of conventional anxiolytics.
MeSH terms
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8-Hydroxy-2-(di-n-propylamino)tetralin / metabolism
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Amnesia / chemically induced
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Amnesia / drug therapy*
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Animals
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Anti-Anxiety Agents / chemical synthesis*
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Anti-Anxiety Agents / metabolism
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Anti-Anxiety Agents / pharmacology
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Avoidance Learning
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Conflict, Psychological
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Male
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Mice
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Molecular Structure
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Pyridines / chemical synthesis*
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Pyridines / metabolism
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Pyridines / pharmacology
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Rats
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Rats, Sprague-Dawley
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Rats, Wistar
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Receptors, Serotonin / metabolism*
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Scopolamine
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Stereoisomerism
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Structure-Activity Relationship
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Thienopyridines
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Thiophenes / chemical synthesis*
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Thiophenes / metabolism
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Thiophenes / pharmacology
Substances
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Anti-Anxiety Agents
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Pyridines
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Receptors, Serotonin
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Thienopyridines
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Thiophenes
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3-((2-hydroxycyclohex-1-yl)aminocarbonyl)-1,2,3,4-tetrahydro(1)benzothieno(2,3-c)pyridine
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3-((benzodioxol-5-yl)methylaminocarbonyl)-1,2,3,4-tetrahydro(1)benzothieno(2.3-c)pyridine
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8-Hydroxy-2-(di-n-propylamino)tetralin
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Scopolamine