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【结 构 式】

【药物名称】

【化学名称】2(S)-Allyl-3(R)-[N-[1(S)-(1H-indol-3-ylcarbonyl)-2-phenylethyl]carbamoyl]-5-methylhexanehydroxamic acid

【CA登记号】

【 分 子 式 】C28H33N3O4

【 分 子 量 】475.59291

【开发单位】Abbott (Originator)

【药理作用】Antiarthritic Drugs, Bone Diseases, Treatment of, METABOLIC DRUGS, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Treatment of Osteoporosis, Matrix Metalloproteinase Inhibitors, TNF-alpha Production Inhibitors

合成路线1

Friedel Crafts acylation of indole (II) with phenylalanine N-carboxyanhydride (I) in the presence of AlCl3 gave aminoketone (III). Subsequent condensation of (III) with the succinate building block (IV) in DMF afforded succinamide (V). Further deprotection of the tert-butyl ester of (V) by treatment with trifluoroacetic acid provided carboxylic acid (VI), which was coupled with O-tert-butyldimethylsilyl hydroxylamine (VII) in the presence of EDC and HOBt to yield, after desilylation, the target hydroxamic acid.

1 Sheppard, G.S.; Florjancic, A.S.; Giesler, J.R.; Xu, L.; Guo, Y.; Davidsen, S.K.; Marcotte, P.A.; Elmore, I.; Albert, D.H.; Terrance, J.M.; Bouska, J.J.; Goodfellow, C.L.; Morgan, D.W.; Summers, J.B.; Aryl ketones as novel replacements for the C-terminal amide bond of succinyl hydroxamate MMP inhibitors. Bioorg Med Chem Lett 1998, 8, 22, 3251.
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) 21645 (4S)-4-benzyl-1,3-oxazolidine-2,5-dione 14825-82-2 C10H9NO3 详情 详情
(II) 15292 Indole; 1H-indole 120-72-9 C8H7N 详情 详情
(III) 21647 (2S)-2-amino-1-(1H-indol-3-yl)-3-phenyl-1-propanone C17H16N2O 详情 详情
(IV) 21641 1-(tert-butyl) 4-(2,3,4,5,6-pentafluorophenyl) (2S,3R)-2-allyl-3-isobutylbutanedioate C21H25F5O4 详情 详情
(IV) 21655 4-(tert-butyl) 1-(2,3,4,5,6-pentafluorophenyl) (2R,3S)-2-isobutyl-3-(4-pentenyl)butanedioate C23H29F5O4 详情 详情
(V) 21649 tert-butyl (2S)-2-[(1R)-1-([[(1S)-1-benzyl-2-(1H-indol-3-yl)-2-oxoethyl]amino]carbonyl)-3-methylbutyl]-4-pentenoate C32H40N2O4 详情 详情
(V) 21656 tert-butyl (2S)-2-[(1R)-1-([[(1S)-1-benzyl-2-(1H-indol-3-yl)-2-oxoethyl]amino]carbonyl)-3-methylbutyl]-6-heptenoate C34H44N2O4 详情 详情
(VI) 21650 (2S)-2-[(1R)-1-([[(1S)-1-benzyl-2-(1H-indol-3-yl)-2-oxoethyl]amino]carbonyl)-3-methylbutyl]-4-pentenoic acid C28H32N2O4 详情 详情
(VI) 21657 (2S)-2-[(1R)-1-([[(1S)-1-benzyl-2-(1H-indol-3-yl)-2-oxoethyl]amino]carbonyl)-3-methylbutyl]-6-heptenoic acid C30H36N2O4 详情 详情
(VII) 21644 (Aminooxy)(tert-butyl)dimethylsilane; O-[tert-Butyl(dimethyl)silyl]hydroxylamine 41879-39-4 C6H17NOSi 详情 详情
Extended Information