|
【结 构 式】 
|
【药物名称】PNU-109230 【化学名称】N-[3-[3-Fluoro-4-[4-(2-hydroxy-1-oxoethyl)piperazin-1-yl]phenyl]-2-oxooxazolidin-5(S)-ylmethyl]-2,2-dichloroacetamide 【CA登记号】 【 分 子 式 】C18H21Cl2FN4O5 【 分 子 量 】463.29627 |
【开发单位】Pfizer (Originator) 【药理作用】Antibacterial Drugs, ANTIINFECTIVE THERAPY, Oxazolidinones |
合成路线1
Hydrogenolysis of PNU-100542 (I) removed the benzyloxycarbonyl group and afforded secondary amine (II), which was acylated with (acetoxy)acetyl chloride (III) in the presence of triethylamine to provide amide PNU-142581 (IV). Then, acetate and phthaloyl protecting groups were both removed on treatment with an hydroalcoholic solution of methylamine, and the resulting aminoalcohol PNU-141718 (V) was N-acylated with dichloroacetyl chloride (VI) to yield the desired amide PNU-109230.
| 【1】 Ulanowicz, D.A.; et al.; Synthesis and biological activity of N-acetyl modified analogs of oxazolidinone anticancer agents linezolid and eperezolid. 37th Intersci Conf Antimicrob Agents Chemother (Sept 28-Oct 1, Toronto) 1997, Abst F-21. |
| 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) | 17824 | benzyl 4-(4-[(5S)-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl)-1-piperazinecarboxylate | C30H27FN4O6 | 详情 | 详情 | |
| (II) | 17825 | 2-([(5S)-3-[3-fluoro-4-(1-piperazinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl)-1H-isoindole-1,3(2H)-dione | C22H21FN4O4 | 详情 | 详情 | |
| (III) | 10456 | Acetoxiacetil chloride; 2-chloro-2-oxoethyl acetate | 13831-31-7 | C4H5ClO3 | 详情 | 详情 |
| (IV) | 17827 | 2-[4-(4-[(5S)-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl)-1-piperazinyl]-2-oxoethyl acetate | C26H25FN4O7 | 详情 | 详情 | |
| (V) | 17828 | (5S)-5-(aminomethyl)-3-[3-fluoro-4-(4-glycoloyl-1-piperazinyl)phenyl]-1,3-oxazolidin-2-one | C16H21FN4O4 | 详情 | 详情 | |
| (VI) | 17829 | 2,2-dichloroacetyl chloride; dichloroacetyl chloride | 79-36-7 | C2HCl3O | 详情 | 详情 |