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【结 构 式】 
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【药物名称】NR58.4 【化学名称】N-[2,6-Dioxopiperidin-3(S)-yl]-10-undecenamide 【CA登记号】284495-31-4 【 分 子 式 】C16H26N2O3 【 分 子 量 】294.39722 |
【开发单位】NeoRx (Originator) 【药理作用】Antiarthritic Drugs, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Cytokine Production Inhibitors, TNF-alpha Production Inhibitors |
合成路线1
The title compound was prepared by two related procedures. The acylation of L-glutamine (I) with 10-undecenoyl chloride (II) under Schotten-Baumann conditions afforded N-undecenoylglutamine (III). This was then cyclized to the title glutarimide derivative by treatment with dicyclohexylcarbodiimide and N-hydroxysuccinimide.
| 【1】 Fox, D.J.; Grainger, D.J.; Reckless, J.; Warren, S.G.; Design, synthesis, and preliminary pharmacological evaluation of N-acyl-3-aminoglutarimides as broad-spectrum chemokine inhibitors in vitro and anti-inflammatory agents in vivo. J Med Chem 2002, 45, 2, 360. |
| 【2】 Grainger, D.J.; Tatalick, L.M. (NeoRx Corp.); Cpds. and methods to inhibit or augment an inflammatory response. WO 0042071 . |
合成路线2
In an alternative synthesis, (S)-3-(tert-butoxycarbonylamino)glutarimide (IV) was deprotected by means of trifluoroacetic acid to yield the aminoglutarimide (V). BOP-mediated coupling of (V) with 10-undecenoic acid (VI) then gave the target amide.
| 【1】 Fox, D.J.; Grainger, D.J.; Reckless, J.; Warren, S.G.; Design, synthesis, and preliminary pharmacological evaluation of N-acyl-3-aminoglutarimides as broad-spectrum chemokine inhibitors in vitro and anti-inflammatory agents in vivo. J Med Chem 2002, 45, 2, 360. |
| 【2】 Grainger, D.J.; Tatalick, L.M. (NeoRx Corp.); Cpds. and methods to inhibit or augment an inflammatory response. WO 0042071 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 27696 | tert-butyl (3S)-2,6-dioxopiperidinylcarbamate | C10H16N2O4 | 详情 | 详情 | |
| (V) | 48171 | (3S)-3-amino-2,6-piperidinedione | C5H8N2O2 | 详情 | 详情 | |
| (VI) | 48172 | Kyselina Undecylenova; n-Undecylenic acid; 10-Henedecenoic acid; Undec-10-enoic acid; 10-Hendecenoic acid; Undecyl-10-enic acid; 10-Hendecenoic; 9-Undecylenic acid; 10-Undecylenic acid; 10-undecenoic acid | 112-38-9 | C11H20O2 | 详情 | 详情 |