N-benzoyl-1,5-benzothiazepine and its S-oxide as vasopressin receptor ligands: insight into the active stereochemistry around the seven-membered ring

Journal of Medicinal Chemistry
Tetsuya YonedaHideaki Natsugari

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.

References

Oct 27, 2005·Journal of the American Chemical Society·Marc PetitDennis P Curran
Oct 10, 2008·Organic Letters·Hidetsugu TabataHideaki Natsugari
Aug 17, 2010·Drug Discovery Today·Punniyakoti T VeeraveeduKenichi Watanabe
May 31, 2013·The Journal of Organic Chemistry·Hidetsugu TabataHideaki Natsugari

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Citations

Jul 17, 2016·European Journal of Medicinal Chemistry·Jun YangXiangbao Meng
May 18, 2021·The Journal of Organic Chemistry·Takuya NambaHideyo Takahashi
Jul 1, 2021·Organic & Biomolecular Chemistry·Lillian A de Ceuninck van CapelleChristopher J T Hyland
Oct 3, 2017·The Journal of Organic Chemistry·Yuka TakahashiTomohiko Ohwada
Nov 26, 2019·The Journal of Organic Chemistry·Hidetsugu TabataHideaki Natsugari
May 6, 2017·Journal of Medicinal Chemistry·Hidetsugu TabataHideaki Natsugari

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