H. Kawakubo et al., )-1,2,3,4-TETRAHYDRO[1]BENZOTHIENO[2,3-C]PYRIDINES - NOVEL OPTICALLY-ACTIVE COMPOUNDS WITH STRONG 5-HT(1A) RECEPTOR-BINDING ABILITY EXHIBITING ANTICONFLICT ACTIVITY AND LESSENING OF MEMORY IMPAIRMENT, Journal of medicinal chemistry, 36(23), 1993, pp. 3526-3532
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 recep
tor while the (S)-isomers have no such ability. The affinity of the (R
)-isomers was discussed on the basis of structure-activity relationshi
ps between the affinity-and hydrophobicity of the (R)-isomers. Compoun
ds 71 and 107, which are representative derivative compounds, have ant
iconflict 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.