• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【药物名称】ONO-BB-039-02

【化学名称】N2-[2(S)-Benzyl-3-sulfanylpropionyl]-L-glutamic acid 1-phenylamide
      4(S)-[3-Phenyl-2(S)-(sulfanylmethyl)propionamido]-5-oxo-5-(phenylamino)pentanoic acid

【CA登记号】126349-24-4

【 分 子 式 】C21H24N2O4S

【 分 子 量 】400.50043

【开发单位】Ono (Originator)

【药理作用】CARDIOVASCULAR DRUGS, Heart Failure Therapy, Enkephalinase Inhibitors, Neprilysin Inhibitors

合成路线1

Chiral resolution of protected dl-thiopropionic acid derivative (I) is performed by first condensation with (1R,2S)-(-)-2-amino-1,2-diphenyl ethanol in acetonitrile followed by diastereomer separation and finally hydrolysis of the optically active salt to afford the desired stereoisomer (S)-(II). Activation of (S)-(II) with oxalyl chloride in dichloromethane and subsequent coupling to L-isoglutamine derivative (III) in CH2Cl2 in the presence of pyridine provides amide (S)-(IV), which is finally converted into the target product by alkaline hydrolysis with LiOH in THF.

1 Katsube, N.; Nakai, H.; Nagao, Y.; Sakai, Y.; Senokuchi, K.; Kawamura, M.; New orally active enkephalinase inhibitors: Their synthesis, biological activity, and analgesic properties. Bioorg Med Chem 1998, 6, 4, 441.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 48898 3-(benzoylsulfanyl)-2-benzylpropionic acid C17H16O3S 详情 详情
(II) 15141 (1R,2S)-(-)-2-Amino-1,2-diphenylethanol; (1S,2R)-2-amino-1,2-diphenyl-1-ethanol 23190-16-1 C14H15NO 详情 详情
(III) 48899 (2S)-3-(benzoylsulfanyl)-2-benzylpropionic acid C17H16O3S 详情 详情
(IV) 48900 benzyl (4S)-4-amino-5-anilino-5-oxopentanoate C18H20N2O3 详情 详情
(V) 48901 benzyl (4S)-5-anilino-4-[[(2S)-3-(benzoylsulfanyl)-2-benzylpropanoyl]amino]-5-oxopentanoate C35H34N2O5S 详情 详情
Extended Information