N-benzoyl-1,5-benzothiazepine and its S-oxide as vasopressin receptor ligands: insight into the active stereochemistry around the seven-membered ring
Yoneda, T; Tabata, H; Tasaka, T; Oshitari, T; Takahashi, H; Natsugari, H
| HERO ID | 2902177 |
|---|---|
| In Press | No |
| Year | 2015 |
| Title | N-benzoyl-1,5-benzothiazepine and its S-oxide as vasopressin receptor ligands: insight into the active stereochemistry around the seven-membered ring |
| Authors | Yoneda, T; Tabata, H; Tasaka, T; Oshitari, T; Takahashi, H; Natsugari, H |
| Journal | Journal of Medicinal Chemistry |
| Volume | 58 |
| Issue | 7 |
| Page Numbers | 3268-3273 |
| 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. |
| Doi | 10.1021/acs.jmedchem.5b00289 |
| Pmid | 25774991 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |