title: N-benzoyl-1,5-benzothiazepine and its S-oxide as vasopressin receptor ligands: insight into the active stereochemistry around the seven-membered ring.
abstract: The stereochemistry of N-benzoyl-1,5-benzothiazepine and its S-oxide derivatives as vasopressin receptor ligands was examined in detail by freezing the conformation with a methyl group at the C6 or C9 of 1,5-benzothiazepine. It was revealed that the active forms recognized by the receptors are (cis,aS) for 1,5-benzothiazepine (5-7)-II and (cis,1S,aS) (syn) for its S-oxide (8-10)-II. The C9-methyl derivative of 1,5-benzothiazepine S-oxide (10-II) was designed and synthesized, achieving the putative active syn-isomer.
authors.affiliation: †Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan.
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Yoneda
authors.affiliation: †Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan.
authors.forename: Hidetsugu
authors.initials: H
authors.lastname: Tabata
authors.affiliation: ‡Affinity Science Corporation, 4-1-1 Akasaka, Minato-ku, Tokyo 107-0052, Japan.
authors.forename: Tomohiko
authors.initials: T
authors.lastname: Tasaka
authors.affiliation: †Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan.
authors.forename: Tetsuta
authors.initials: T
authors.lastname: Oshitari
authors.affiliation: †Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan.
authors.forename: Hideyo
authors.initials: H
authors.lastname: Takahashi
authors.affiliation: †Faculty of Pharma Sciences, Teikyo University, 2-11-1 Kaga, Itabashi-ku, Tokyo 173-8605, Japan.
authors.forename: Hideaki
authors.initials: H
authors.lastname: Natsugari
mesh_terms: D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D006801:Humans; D008024:Ligands; D008968:Molecular Conformation; D010087:Oxides / Q000737:chemistry; D017483:Receptors, Vasopressin / Q000378:metabolism*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013841:Thiazepines / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D008024:Ligands; D010087:Oxides; D017483:Receptors, Vasopressin; D013841:Thiazepines