title: (R)-1,2,3,4-tetrahydro[1]benzothieno[2,3-c]pyridines: novel optically active compounds with strong 5-HT1A receptor binding ability exhibiting anticonflict activity and lessening of memory impairment.
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.
authors.affiliation: Synthetic Section, Asahi Chemical Industry Company, Ltd., Miyazaki, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Kawakubo
authors.forename: S
authors.initials: S
authors.lastname: Takagi
authors.forename: Y
authors.initials: Y
authors.lastname: Yamaura
authors.forename: S
authors.initials: S
authors.lastname: Katoh
authors.forename: Y
authors.initials: Y
authors.lastname: Ishimoto
authors.forename: T
authors.initials: T
authors.lastname: Nagatani
authors.forename: D
authors.initials: D
authors.lastname: Mochizuki
authors.forename: T
authors.initials: T
authors.lastname: Kamata
authors.forename: Y
authors.initials: Y
authors.lastname: Sasaki
mesh_terms: D017371:8-Hydroxy-2-(di-n-propylamino)tetralin / Q000378:metabolism; D000647:Amnesia / Q000139:chemically induced / Q000188:drug therapy*; D000818:Animals; D014151:Anti-Anxiety Agents / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D001362:Avoidance Learning; D003220:Conflict, Psychological; D008297:Male; D051379:Mice; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D051381:Rats; D017207:Rats, Sprague-Dawley; D017208:Rats, Wistar; D011985:Receptors, Serotonin / Q000378:metabolism*; D012601:Scopolamine; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D058924:Thienopyridines; D013876:Thiophenes / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology
chemical_list: D014151:Anti-Anxiety Agents; D011725:Pyridines; D011985:Receptors, Serotonin; D058924:Thienopyridines; D013876:Thiophenes; C084466:3-((2-hydroxycyclohex-1-yl)aminocarbonyl)-1,2,3,4-tetrahydro(1)benzothieno(2,3-c)pyridine; C084467:3-((benzodioxol-5-yl)methylaminocarbonyl)-1,2,3,4-tetrahydro(1)benzothieno(2.3-c)pyridine; D017371:8-Hydroxy-2-(di-n-propylamino)tetralin; D012601:Scopolamine