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

【结 构 式】

【药物名称】OPB-3206

【化学名称】3(R)-Isobutyl-4-[1-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-3(S)-ylamino]-4-oxobutyrohydroxamic acid

【CA登记号】

【 分 子 式 】C18H25N3O5

【 分 子 量 】363.41705

【开发单位】Otsuka (Originator)

【药理作用】ONCOLYTIC DRUGS, Matrix Metalloproteinase Inhibitors

合成路线1

The protection of the amino group of 3(S)-amino-1-hydroxy-1,2,3,4-tetrahydroquinolin-2-one (I) with tert-butoxycarbonyl anhydride gives the carbamate (II), which is methylated with NaH and methyl iodide in DMF yielding the N-methoxy derivative (III). The deprotection of (III) with TFA and its condensation with 2(R)-isobutylsuccinic acid 4-tert-butyl monoester (IV) by means of DCC and HOBT in DMF affords the succinamic ester (V), which is hydrolyzed with TFA to give the succinamic acid (VI). The reaction of (VI) with O-benzylhydroxylamine by means of HOBT in DMF yields the benzyl hydroxamate (VII), which is finally debenzylated by hydrogenation with H2 over Pd/C in ethanol.

1 Sakamoto, M.; Imaoka, T.; Motoyama, M.; Yamamoto, Y.; Takasu, H. (Otsuka Pharmaceutical Co., Ltd.); Carbostyril derivs. as matrix metalloproteinases inhibitors. EP 0641323; JP 1995157470; WO 9421612 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
40671 1-[(hydroxyamino)methyl]benzene; N-benzylhydroxylamine C7H9NO 详情 详情
(I) 30951 (3S)-3-amino-1-hydroxy-3,4-dihydro-2(1H)-quinolinone C9H10N2O2 详情 详情
(II) 30952 tert-butyl (3S)-1-hydroxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinylcarbamate C14H18N2O4 详情 详情
(III) 30953 tert-butyl (3S)-1-methoxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinylcarbamate C15H20N2O4 详情 详情
(IV) 25393 (2R)-2-[2-(tert-butoxy)-2-oxoethyl]-4-methylpentanoic acid C12H22O4 详情 详情
(V) 30954 tert-butyl (3R)-3-([[(3S)-1-methoxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]amino]carbonyl)-5-methylhexanoate C22H32N2O5 详情 详情
(VI) 30955 (3R)-3-([[(3S)-1-methoxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]amino]carbonyl)-5-methylhexanoic acid C18H24N2O5 详情 详情
(VII) 30956 (2R)-N(4)-(benzyloxy)-2-isobutyl-N(1)-[(3S)-1-methoxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]butanediamide C25H31N3O5 详情 详情
Extended Information